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122-00-9

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122-00-9 Usage

Description

4'-Methylacetophenone has a fruity, floral odor resembling acetophenone and a sweet, strawberry-like flavor. May be prepared by slow addition of acetyl chloride to a mixture of toluene and AlCl in an ice bath and under vacuum, maintaining the temperature at +5°C and then letting it increase to +20°C.

Chemical Properties

Different sources of media describe the Chemical Properties of 122-00-9 differently. You can refer to the following data:
1. 4?-Methylacetophenone has a fruity, floral odor resembling acetophenone and a sweet, strawberry-like flavor.
2. clear colourless to pale yellowish liquid
3. 4'-Methylacetophenone has been identified in Brazilian rosewood oil and in pepper. It occurs as colorless crystals with a floral, sweet odor that is milder than that of acetophenone. 4-Methylacetophenone is prepared from toluene and acetic anhydride or acetyl chloride by a Friedel–Crafts reaction. It is used for blossom notes in mimosaand hawthorn-type perfumes, especially soap perfumes.

Occurrence

Reported found in the essential oil distilled from the wood of Myrocarpus fastigiatus, Myrocarpus frondo sus, Bois de Rose. Also reported found in sour cherry, orange and grapefruit peel oil, black currants, guava, peach, blackberry, celery, potato, tomato, mentha oils, pepper, parsley, smoked fish, cognac, parmesan cheese, cocoa, tea, soybean, cloudberry, mango, cauliflower, broccoli, rice bran, buckwheat, dried bonito, cherimoya, calabash nutmeg and mastic gum leaf oil, cooked cabbage, mandarin juice.

Uses

Different sources of media describe the Uses of 122-00-9 differently. You can refer to the following data:
1. 4'-Methylacetophenone is a methylated acteophenone used in cosmetics and perfumery. The presence of 4'-Methylacetophenone has been shown to accelerate the photopolymerization of Methyl methacrylate.
2. 4'-Methylacetophenone is used as a flavoring agent. It reacts with morpholine to get 4-(p-tolyl-thioacetyl)-morpholine in the presence of sulfur as a reagent. Further, it is used as an intermediate in the manufacture of active pharmaceutical ingredients, perfumes and cosmetics.

Preparation

By slow addition of acetyl chloride to a mixture of toluene and AlCl in an ice bath and under vacuum, maintaining the temperature at +5°C and then letting it increase to +20°C.

Taste threshold values

Taste characteristics at 20 ppm: sweet, creamy, fruity, cherry and heliotropine-like.

Synthesis Reference(s)

Journal of the American Chemical Society, 110, p. 2560, 1988 DOI: 10.1021/ja00216a032Tetrahedron Letters, 27, p. 2965, 1986 DOI: 10.1016/S0040-4039(00)84691-2

General Description

4′-Methylacetophenone occurs naturally in mango, tomato and orange.

Safety Profile

Moderately toxic by ingestion. A human skin irritant. A flammable liquid. When heated to decomposition it emits acrid smoke and irritating fumes. See also KETONES.

Purification Methods

Impurities, including the o-and m-isomers, are removed by forming the semicarbazone (m 212-213.5o) which, after repeated crystallisation, is hydrolysed to the ketone. [Brown & Marino J Am Chem Soc 84 1236 1962.] It can also be purified by distillation under reduced pressure, followed by low temperature crystallisation from isopentane. [Beilstein 7 IV 701.]

Check Digit Verification of cas no

The CAS Registry Mumber 122-00-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 2 respectively; the second part has 2 digits, 0 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 122-00:
(5*1)+(4*2)+(3*2)+(2*0)+(1*0)=19
19 % 10 = 9
So 122-00-9 is a valid CAS Registry Number.

122-00-9 Well-known Company Product Price

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  • Alfa Aesar

  • (A14469)  4'-Methylacetophenone, 96%   

  • 122-00-9

  • 50g

  • 245.0CNY

  • Detail
  • Alfa Aesar

  • (A14469)  4'-Methylacetophenone, 96%   

  • 122-00-9

  • 250g

  • 448.0CNY

  • Detail
  • Alfa Aesar

  • (A14469)  4'-Methylacetophenone, 96%   

  • 122-00-9

  • 1000g

  • 1277.0CNY

  • Detail

122-00-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 4'-Methylacetophenone

1.2 Other means of identification

Product number -
Other names 4’-Methylacetophenone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:122-00-9 SDS

122-00-9Synthetic route

4-(bromoacetyl)toluene
619-41-0

4-(bromoacetyl)toluene

para-methylacetophenone
122-00-9

para-methylacetophenone

Conditions
ConditionsYield
With AcrH2; perchloric acid; tris(2,2’-bipyridine)ruthenium(II) In acetonitrile at 298℃; for 8h; Irradiation;100%
With AcrH2; perchloric acid; tris(2,2’-bipyridine)ruthenium(II) In acetonitrile at 298℃; for 8h; Quantum yield; Mechanism; Irradiation; Electron-Transfer Rate Constants ;;100%
With ammonium chloride; zinc In ethanol at 80℃; for 0.00833333h; microwave irradiation;99%
4-n-methylphenylacetylene
766-97-2

4-n-methylphenylacetylene

para-methylacetophenone
122-00-9

para-methylacetophenone

Conditions
ConditionsYield
With gold(III) tribromide; water at 200℃; for 0.333333h; microwave irradiation;100%
With water at 59.84℃; for 24h; Ionic liquid;100%
With iron(III) chloride; air; water; 1,2-dichloro-ethane at 75℃; for 30h; regioselective reaction;99%
4-methyl-N'-(1-(p-tolyl)ethylidene)benzenesulfonohydrazide

4-methyl-N'-(1-(p-tolyl)ethylidene)benzenesulfonohydrazide

para-methylacetophenone
122-00-9

para-methylacetophenone

Conditions
ConditionsYield
With tert.-butylhydroperoxide In acetone for 10h; Heating;100%
With phosphoric acid for 0.0166667h; microwave irradiation;76%
4-methylethylbenzene
622-96-8

4-methylethylbenzene

para-methylacetophenone
122-00-9

para-methylacetophenone

Conditions
ConditionsYield
With potassium permanganate; iron(III) chloride In acetone at -78 - 20℃; for 16h;100%
With tert.-butylhydroperoxide; 1-n-butyl-3-methylimidazolim bromide In water at 20℃; for 12h;92%
With oxygen In water for 4h; Reflux;90%
dimethyl zinc(II)
544-97-8

dimethyl zinc(II)

para-bromoacetophenone
99-90-1

para-bromoacetophenone

para-methylacetophenone
122-00-9

para-methylacetophenone

Conditions
ConditionsYield
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane for 1h; Heating;100%
CH3C6H4CH(CH3)OH
536-50-5

CH3C6H4CH(CH3)OH

para-methylacetophenone
122-00-9

para-methylacetophenone

Conditions
ConditionsYield
With iodine; potassium carbonate In tert-butyl alcohol at 90℃; for 5h;99%
With silica-supported Jones reagent In dichloromethane for 0.00269444h;99.5%
With C53H46ClN3P2Ru; potassium tert-butylate; acetone at 56℃; under 750.075 Torr; for 0.166667h; Oppenauer Oxidation;99%
acetyl chloride
75-36-5

acetyl chloride

toluene
108-88-3

toluene

para-methylacetophenone
122-00-9

para-methylacetophenone

Conditions
ConditionsYield
With aluminum (III) chloride In chloroform at 0 - 20℃; Inert atmosphere;99%
With iron(III) oxide at 20℃; for 0.133333h; Friedel Crafts acylation; regioselective reaction;96%
With iron oxide In neat (no solvent) at 20℃; for 0.05h; Friedel-Crafts Acylation; Green chemistry;96%
1-ethenyl-4-methylbenzene
622-97-9

1-ethenyl-4-methylbenzene

para-methylacetophenone
122-00-9

para-methylacetophenone

Conditions
ConditionsYield
With water; oxygen In methanol; dimethyl sulfoxide at 80℃; under 1520.1 Torr; for 20h; Wacker Oxidation; Autoclave;98%
With tert.-butylhydroperoxide; C21H19N5Pd(2+)*2BF4(1-) In decane; acetonitrile at 45℃; for 12h; Wacker Oxidation;98%
With dihydrogen peroxide In water; acetonitrile at 55℃; for 12h; Wacker Oxidation;97%
acetyl chloride
75-36-5

acetyl chloride

toluene
108-88-3

toluene

A

para-methylacetophenone
122-00-9

para-methylacetophenone

B

2-Methylacetophenone
577-16-2, 122382-54-1

2-Methylacetophenone

Conditions
ConditionsYield
With aluminium trichloride; 1-ethyl-3-methyl-1H-imidazol-3-ium chloride at 20℃; for 1h;A 98%
B 1%
iron oxide for 6h; Ambient temperature; Yield given;A n/a
B 3%
With silver trifluoromethanesulfonate 1) CH2Cl2, -50 deg C, 15 h, 2) CH2Cl2, -40 deg C, 2,5 h; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;
4-methylacethophenone oxime
2089-33-0

4-methylacethophenone oxime

para-methylacetophenone
122-00-9

para-methylacetophenone

Conditions
ConditionsYield
With water; oxygen In acetonitrile at 60℃; under 760.051 Torr; for 2h; Autoclave; Green chemistry;97%
With sodium nitrite In water; acetonitrile at 40℃; for 1.33333h;97%
With Dess-Martin periodane In dichloromethane; water for 0.25h;96%
Acetyl bromide
506-96-7

Acetyl bromide

toluene
108-88-3

toluene

A

para-methylacetophenone
122-00-9

para-methylacetophenone

B

2-Methylacetophenone
577-16-2, 122382-54-1

2-Methylacetophenone

C

3-Methylacetophenone
585-74-0

3-Methylacetophenone

Conditions
ConditionsYield
With iron(II) sulfate for 2h; Product distribution; Ambient temperature; other aromatic hydrocarbon, acetylating reagents, catalyst, reaction times and temperature;A 97%
B 2%
C 1%
CH3C6H4CH(CH3)OH
536-50-5

CH3C6H4CH(CH3)OH

3,3-dimethyldioxirane
74087-85-7

3,3-dimethyldioxirane

A

2-hydroxy-1-p-tolyl-ethanone
4079-54-3

2-hydroxy-1-p-tolyl-ethanone

B

para-methylacetophenone
122-00-9

para-methylacetophenone

Conditions
ConditionsYield
In acetone at 25℃; for 3h;A 2%
B 97%
In acetone at 25℃; for 3h; Thermodynamic data; Rate constant; Ea, ΔH(excit.), ΔS(excit.), ΔG(excit.);A 2%
B 97%
p-methyl acetophenone semicarbazone
3352-98-5

p-methyl acetophenone semicarbazone

para-methylacetophenone
122-00-9

para-methylacetophenone

Conditions
ConditionsYield
With CuCl2*2H2O for 0.00166667h; microwave irradiation;96%
With potassium permanganate; montmorillonite K-10 for 0.166667h;95%
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; water; silica gel In dichloromethane at 20℃; for 2h;92%
1-(4-methylphenyl)ethyl trimethylsilyl ether
128816-30-8

1-(4-methylphenyl)ethyl trimethylsilyl ether

para-methylacetophenone
122-00-9

para-methylacetophenone

Conditions
ConditionsYield
With N-benzyl-N,N-dimethyl anilinium peroxodisulfate In acetonitrile for 0.166667h; Reflux;96%
toluene-4-sulfonic acid hydrazide
1576-35-8

toluene-4-sulfonic acid hydrazide

acetonitrile
75-05-8

acetonitrile

para-methylacetophenone
122-00-9

para-methylacetophenone

Conditions
ConditionsYield
With 1,10-Phenanthroline; water; palladium diacetate at 100℃; under 760.051 Torr; for 6h;96%
-butyl vinyl ether
111-34-2

-butyl vinyl ether

para-bromotoluene
106-38-7

para-bromotoluene

para-methylacetophenone
122-00-9

para-methylacetophenone

Conditions
ConditionsYield
Stage #1: -butyl vinyl ether; para-bromotoluene With meso-2,4-bis(diphenylphosphino)pentane; triethylamine; palladium diacetate In dimethyl sulfoxide at 115℃; for 36h; Heck arylation;
Stage #2: With hydrogenchloride In dimethyl sulfoxide at 20℃;
95%
Stage #1: -butyl vinyl ether; para-bromotoluene With palladium diacetate; 1,3-bis-(diphenylphosphino)propane; triethylamine In various solvent(s) at 120℃; for 36h; Heck reaction;
Stage #2: With hydrogenchloride Further stages.;
88%
With 1,3-bis-(diphenylphosphino)propane; diisopropylamine; 1-butyl-3-methylimidazolium Tetrafluoroborate; palladium diacetate In dimethyl sulfoxide at 115℃; for 24h; Heck arylation;87%
With hydrogenchloride; palladium diacetate; 1,3-bis-(diphenylphosphino)propane; thallium(I) acetate; triethylamine 1) DMF, 100 deg C, 6 h; 2) room temp., 1 h; Yield given. Multistep reaction;
C21H18N6
111508-08-8

C21H18N6

para-methylacetophenone
122-00-9

para-methylacetophenone

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran for 10h; Ambient temperature;95%
(Z)-2-(4,5-Dihydro-oxazol-2-yl)-1-p-tolyl-vinylamine
143407-58-3

(Z)-2-(4,5-Dihydro-oxazol-2-yl)-1-p-tolyl-vinylamine

para-methylacetophenone
122-00-9

para-methylacetophenone

Conditions
ConditionsYield
With sulfuric acid at 100℃; for 6h;95%
4-methylacetophenone hydrazone
64252-53-5

4-methylacetophenone hydrazone

para-methylacetophenone
122-00-9

para-methylacetophenone

Conditions
ConditionsYield
With ammonium dichromate(VI); water; silica gel; zirconium(IV) chloride at 80℃; for 0.583333h;95%
With [(NO3)3Ce]3.H2IO6 In acetonitrile for 0.5h; Heating;85%
With water; silica gel; iodic acid for 0.166667h;73%
1-methyl-4-isopropenylbenzene
1195-32-0

1-methyl-4-isopropenylbenzene

para-methylacetophenone
122-00-9

para-methylacetophenone

Conditions
ConditionsYield
With monoethylene glycol diethyl ether at 90℃; for 12h; Green chemistry;95%
With 4,4'-dimethoxyphenyl disulfide; oxygen In acetonitrile at 25℃; under 750.075 Torr; for 16h; Irradiation;90.7%
With tert.-butylhydroperoxide; 2.9-dimethyl-1,10-phenanthroline; copper(II) choride dihydrate In water at 20℃; for 0.5h; Green chemistry;89%
lithium methyltriolborate

lithium methyltriolborate

para-bromoacetophenone
99-90-1

para-bromoacetophenone

para-methylacetophenone
122-00-9

para-methylacetophenone

Conditions
ConditionsYield
With palladium diacetate; ruphos In methanol; water at 80℃; for 12h; Inert atmosphere;95%
trimethyl indium
3385-78-2

trimethyl indium

4-methyl-benzoyl chloride
874-60-2

4-methyl-benzoyl chloride

para-methylacetophenone
122-00-9

para-methylacetophenone

Conditions
ConditionsYield
With mesoporous MCM-41-immobilized phosphine-free heterogeneous palladium(0)-schiff base complex In tetrahydrofuran at 68℃; for 2h; Inert atmosphere; Green chemistry;95%
4-methyl-1-methoxyethylbenzene
79744-75-5

4-methyl-1-methoxyethylbenzene

para-methylacetophenone
122-00-9

para-methylacetophenone

Conditions
ConditionsYield
With dihydrogen peroxide; bromine In dichloromethane; water at 20℃; for 24h;94%
With 3,3-dimethyldioxirane In acetone at 25℃; Rate constant;84 % Spectr.
para-bromoacetophenone
99-90-1

para-bromoacetophenone

trimethyl indium
3385-78-2

trimethyl indium

para-methylacetophenone
122-00-9

para-methylacetophenone

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran for 1h; Heating;94%
methylmagnesium bromide
75-16-1

methylmagnesium bromide

p-Toluic acid
99-94-5

p-Toluic acid

para-methylacetophenone
122-00-9

para-methylacetophenone

Conditions
ConditionsYield
Stage #1: p-Toluic acid With N,O-dimethylhydroxylamine*hydrochloride; N-ethyl-N,N-diisopropylamine; (bis-(2-methoxyethyl)amino)sulfur trufluoride In tetrahydrofuran; dichloromethane at 20℃; for 0.25h;
Stage #2: methylmagnesium bromide In tetrahydrofuran; diethyl ether; dichloromethane at 0℃; for 2h;
94%
1-ethenyl-2-pyrrolidinone
88-12-0

1-ethenyl-2-pyrrolidinone

4-methylphenylboronic acid
5720-05-8

4-methylphenylboronic acid

para-methylacetophenone
122-00-9

para-methylacetophenone

Conditions
ConditionsYield
Stage #1: 1-ethenyl-2-pyrrolidinone; 4-methylphenylboronic acid With 2.9-dimethyl-1,10-phenanthroline; p-benzoquinone; palladium diacetate In acetonitrile at 100℃; for 0.166667h; Heck reaction; microwave irradiation;
Stage #2: With silica gel In ethyl acetate Further stages.;
94%
2-(dimethylamino)-1-(p-tolyl)ethan-1-one
80354-58-1

2-(dimethylamino)-1-(p-tolyl)ethan-1-one

para-methylacetophenone
122-00-9

para-methylacetophenone

Conditions
ConditionsYield
With acetic acid; zinc at 20℃; for 1h;94%
2-phenoxy-1-p-tolylethanone
19513-79-2

2-phenoxy-1-p-tolylethanone

para-methylacetophenone
122-00-9

para-methylacetophenone

Conditions
ConditionsYield
With 2,6-bis[1-(2,6-dimethylphenylimino)ethyl]pyridine cobalt(II)dichloride; bis(pinacol)diborane; sodium t-butanolate In tetrahydrofuran; methanol at 65℃; for 3h; Schlenk technique; Inert atmosphere;94%
1-p-tolyl-ethanone-E-semicarbazone
120445-91-2

1-p-tolyl-ethanone-E-semicarbazone

para-methylacetophenone
122-00-9

para-methylacetophenone

Conditions
ConditionsYield
With hydrogenchloride; Tonsil In ethyl acetate for 1.5h; Heating;93.3%
bismuth(III) chloride In tetrahydrofuran; water for 0.166667h; catalysed cleavage; microwave irradiation;80%
With ammonium persulfate; montmorrilonite K10 clay In solid for 0.0333333h; Irradiation; microwave irradiation;69%
para-methylacetophenone
122-00-9

para-methylacetophenone

1,3,5-tris(4-methyl-phenyl)-benzene
50446-43-0

1,3,5-tris(4-methyl-phenyl)-benzene

Conditions
ConditionsYield
With trichloro(trifluoromethanesulfonato)titanium(IV) at 90 - 100℃; for 10h;100%
With [Cp2Zr(OSO2C8F17)2]*3H2O*THF In toluene at 110℃; for 3.5h;95%
With trifluorormethanesulfonic acid; oxygen In neat (no solvent) at 120℃; for 12h; Green chemistry; chemoselective reaction;93%
para-methylacetophenone
122-00-9

para-methylacetophenone

1-p-tolylethanone oxime
54582-23-9

1-p-tolylethanone oxime

Conditions
ConditionsYield
With hydroxylamine hydrochloride; sodium acetate In methanol Heating;100%
With hydroxylamine hydrochloride; sodium acetate In methanol; water Reflux;100%
With hydroxylamine hydrochloride; sodium acetate In ethanol; water Reflux;99%
para-methylacetophenone
122-00-9

para-methylacetophenone

(S)-1-(4-Methylphenyl)ethanol
536-50-5, 5788-09-0, 42070-92-8, 51154-54-2

(S)-1-(4-Methylphenyl)ethanol

Conditions
ConditionsYield
With Trimethyl borate; dimethylsulfide borane complex; (R)-α,α-diphenylprolinol In toluene at 20℃; for 9h; Inert atmosphere;100%
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; (R)-N-(3-methylpyridine-2-methyl)-7-bis-(3,5-di-tert-butylphenyl)phosphino-7′-amino-1,1′-spirodihydroindane; potassium tert-butylate; hydrogen In ethanol at 25 - 30℃; under 7600.51 Torr; for 0.833333h; Autoclave; optical yield given as %ee; enantioselective reaction;99%
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; (R)-7′-bis-(3,5-di-tert-butylphenyl)phosphino-7′-amino-1,1′-spiroindene; potassium tert-butylate; hydrogen In propan-1-ol at 25 - 30℃; under 4560.31 Torr; for 3h; Autoclave; optical yield given as %ee; enantioselective reaction;99%
ethyl trifluoroacetate,
383-63-1

ethyl trifluoroacetate,

para-methylacetophenone
122-00-9

para-methylacetophenone

4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione
720-94-5

4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione

Conditions
ConditionsYield
With sodium In ethanol at 20℃; for 3.2h; Temperature;100%
With potassium carbonate In isopropyl alcohol; acetonitrile at 40℃; for 24h; Temperature; Solvent;99.08%
With tert-butyl methyl ether; sodium ethanolate In ethanol at 25℃; for 24h; Claisen Condensation; Inert atmosphere;99.8%
para-methylacetophenone
122-00-9

para-methylacetophenone

4-methylacethophenone oxime
2089-33-0

4-methylacethophenone oxime

Conditions
ConditionsYield
With hydroxylamine hydrochloride; sodium acetate In ethanol; water Reflux;100%
With hydroxylamine hydrochloride; sodium acetate In ethanol; water at 95℃;100%
With hydroxylamine hydrochloride; sodium acetate In ethanol; water at 20℃; for 1.5h; Reflux;100%
tetraallyl tin
7393-43-3

tetraallyl tin

para-methylacetophenone
122-00-9

para-methylacetophenone

2-(4-methylphenyl)-4-penten-2-ol
110577-96-3, 110577-98-5, 99288-98-9

2-(4-methylphenyl)-4-penten-2-ol

Conditions
ConditionsYield
2,6-dimethylpyridine; zinc trifluoromethanesulfonate In dichloromethane at 20℃; for 24h;100%
polyaniline-supported Sc In dichloromethane at 20℃; for 3.66667h;95%
With gadolinium(III) chloride In acetonitrile at 20℃; for 3h;88%
With C20H32N2O10 In water at 25℃; for 24h;72%
para-methylacetophenone
122-00-9

para-methylacetophenone

(R)-1-(4-methylphenyl)ethanol
42070-92-8

(R)-1-(4-methylphenyl)ethanol

Conditions
ConditionsYield
With formic acid; C37H38ClN2O2RhS; triethylamine In neat (no solvent) at 24 - 30℃; for 22h; Reagent/catalyst; Inert atmosphere; enantioselective reaction;100%
With dimethylsulfide borane complex; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole In tetrahydrofuran; toluene at 0 - 20℃; for 1h;100%
With potassium tert-butylate; hydrogen; [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II); (R)-Ph-BINAN-H-Py In isopropyl alcohol at 25℃; under 38000 Torr; for 15h;99%
para-methylacetophenone
122-00-9

para-methylacetophenone

trifluoroacetic acid
76-05-1

trifluoroacetic acid

4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione
720-94-5

4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione

Conditions
ConditionsYield
Stage #1: para-methylacetophenone With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Inert atmosphere;
Stage #2: trifluoroacetic acid In tetrahydrofuran; mineral oil at 20℃; for 5h; Inert atmosphere;
100%
With sodium In methanol at 20 - 80℃; for 10h;95%
para-methylacetophenone
122-00-9

para-methylacetophenone

methylamine
74-89-5

methylamine

N-methyl-[1-(4'-methylphenyl)ethylidene]amine
53370-98-2

N-methyl-[1-(4'-methylphenyl)ethylidene]amine

Conditions
ConditionsYield
In ethanol at 20℃; for 48h; Molecular sieve; Inert atmosphere;100%
In ethanol at 20℃; for 48h; Inert atmosphere; Molecular sieve;
In ethanol at 20℃; Molecular sieve; Inert atmosphere; Schlenk technique;
In ethanol at 125℃; for 1.25h; Microwave irradiation;
In ethanol at 20℃; for 96h; Schlenk technique; Sealed tube; Inert atmosphere; Molecular sieve;
4,7-dichloroisatin
18711-13-2

4,7-dichloroisatin

para-methylacetophenone
122-00-9

para-methylacetophenone

4,7-dichloro-3-hydroxyl-3-(2-oxo-2-p-tolylethyl)-1,3-dihydroindol-2-one
1037184-43-2

4,7-dichloro-3-hydroxyl-3-(2-oxo-2-p-tolylethyl)-1,3-dihydroindol-2-one

Conditions
ConditionsYield
With diethylamine In methanol at 20℃;100%
N-butylamine
109-73-9

N-butylamine

para-methylacetophenone
122-00-9

para-methylacetophenone

C13H19N

C13H19N

Conditions
ConditionsYield
With titanium tetrachloride In diethyl ether; dichloromethane at 20℃;100%
In benzene at 70℃; for 6h; Molecular sieve;
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

aniline
62-53-3

aniline

para-methylacetophenone
122-00-9

para-methylacetophenone

α,4-dimethyl-α-(phenylamino)benzeneacetonitrile

α,4-dimethyl-α-(phenylamino)benzeneacetonitrile

Conditions
ConditionsYield
With polymer-supported gallium(III) bis(trifluoromethanesulfonate) In dichloromethane at 40℃; under 15001.5 Torr; for 1h; Strecker reaction; Microreactor;99.6%
With sulfated tungstate at 20℃; for 6h; Strecker reaction; Neat (no solvent);96%
With {Cd2(5-(1-{[4-(3,5-dicarboxylatophenyl)-3,5-dimethyl-1H-pyrazol-1-yl]methyl}-3,5-dimethyl-1H-pyrazol-4-yl)benzene-1,3-dicarboxylate)*x(N,N-dimethylformamide)*yH2O}n at 25℃; for 4h; Inert atmosphere; Schlenk technique;94%
4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

para-methylacetophenone
122-00-9

para-methylacetophenone

4,4'-Dimethylchalcon
21551-47-3

4,4'-Dimethylchalcon

Conditions
ConditionsYield
With sodium hydroxide for 0.0833333h; Product distribution; Ambient temperature;99%
With sodium hydroxide In ethanol at 5 - 10℃;95%
With sulfuric acid In 1,4-dioxane at 90℃; for 2h; Inert atmosphere;91%
para-methylacetophenone
122-00-9

para-methylacetophenone

benzyl alcohol
100-51-6

benzyl alcohol

4-methylphenyl phenethyl ketone
5012-90-8

4-methylphenyl phenethyl ketone

Conditions
ConditionsYield
With potassium phosphate tribasic trihydrate; C39H32Cl2N5PRu In tert-Amyl alcohol at 120℃; for 4h; Inert atmosphere; Schlenk technique;99%
With (1,4-dimethyl-5,7-diphenyl-1,2,3,4-tetrahydro-6H-cyclopenta[b]pyrazin-6-one)(triphenylphosphine)(dicarbonyl)iron; caesium carbonate In toluene at 90℃; for 16h; Schlenk technique; Inert atmosphere;98%
With lithium hydroxide at 140℃; for 48h; Reagent/catalyst; Inert atmosphere;98%
para-methylacetophenone
122-00-9

para-methylacetophenone

CH3C6H4CH(CH3)OH
536-50-5

CH3C6H4CH(CH3)OH

Conditions
ConditionsYield
With LaCu0.67Si1.33; hydrogen In methanol at 120℃; under 22502.3 Torr; for 10h; Autoclave;99%
With formic acid; C18H24ClIrN3 In water at 80℃; for 4h; Schlenk technique; Inert atmosphere; chemoselective reaction;99%
With hydrogen In ethanol at 20℃; for 5h;99%
para-methylacetophenone
122-00-9

para-methylacetophenone

4-methylethylbenzene
622-96-8

4-methylethylbenzene

Conditions
ConditionsYield
With palladium dichloride In methanol at 40℃; for 24h; Inert atmosphere; Green chemistry; chemoselective reaction;99%
With hydrogen In 1,4-dioxane at 200℃; under 15001.5 Torr;98.9%
Stage #1: para-methylacetophenone With iron(III) chloride In methanol at 20℃; for 0.05h;
Stage #2: In methanol at 20℃; for 0.166667h; chemoselective reaction;
98%
para-methylacetophenone
122-00-9

para-methylacetophenone

p-Toluic acid
99-94-5

p-Toluic acid

Conditions
ConditionsYield
With oxygen; copper(II) nitrate In acetonitrile at 120℃; under 4500.45 Torr; for 10h;99%
With copper(II) nitrate trihydrate; oxygen In acetonitrile at 120℃; under 4500.45 Torr; for 10h; Autoclave;97%
With sodium hydroxide; sodium bromite; sodium bromide In water for 6h; Ambient temperature;96%
4-methylbenzoic acid ethyl ester
94-08-6

4-methylbenzoic acid ethyl ester

para-methylacetophenone
122-00-9

para-methylacetophenone

1,3-bis(p-methylphenyl)-1,3-propanedione
3594-36-3

1,3-bis(p-methylphenyl)-1,3-propanedione

Conditions
ConditionsYield
With sodium hydroxide99%
With sodium hydride In tetrahydrofuran; mineral oil at 0 - 40℃; for 17h; Inert atmosphere;80%
With sodium hydride In benzene for 10h;66%
With sodium hydride In tetrahydrofuran; mineral oil Inert atmosphere; Reflux;33%
Claisen condensation;
Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

para-methylacetophenone
122-00-9

para-methylacetophenone

1-methyl-4-isopropenylbenzene
1195-32-0

1-methyl-4-isopropenylbenzene

Conditions
ConditionsYield
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran at 0℃; for 1h; Inert atmosphere;
Stage #2: para-methylacetophenone In tetrahydrofuran at 20℃; Inert atmosphere;
99%
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 1h; Wittig Olefination; Inert atmosphere;
Stage #2: para-methylacetophenone In tetrahydrofuran; hexane at 0 - 23℃; for 18h; Wittig Olefination; Inert atmosphere;
88%
Stage #1: Methyltriphenylphosphonium bromide With sodium hydride In tetrahydrofuran at 70℃; for 0.8h;
Stage #2: para-methylacetophenone In tetrahydrofuran at 75℃; for 10h; Temperature; Cooling with ice;
80%
para-methylacetophenone
122-00-9

para-methylacetophenone

p-methylphenacyl chloride
4209-24-9

p-methylphenacyl chloride

Conditions
ConditionsYield
With N,N,N-trimethylbenzenemethanaminium dichloroiodate In methanol; 1,2-dichloro-ethane for 3h; Heating;99%
With 1,3-dichloro-5,5-dimethylhydantoin; silica gel In methanol for 1h; Reflux;92%
With tetrachlorosilane; urea hydrogen peroxide adduct In dichloromethane at 0℃; for 1h;92%
[bis(acetoxy)iodo]benzene
3240-34-4

[bis(acetoxy)iodo]benzene

para-methylacetophenone
122-00-9

para-methylacetophenone

2-oxo-2-(4-tolyl)ethyl acetate
65143-37-5

2-oxo-2-(4-tolyl)ethyl acetate

Conditions
ConditionsYield
With acetic acid; scandium tris(trifluoromethanesulfonate) at 50℃; for 48h;99%
With acetic anhydride; acetic acid
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

para-methylacetophenone
122-00-9

para-methylacetophenone

2-(4-tolyl)-2-(trimethylsiloxy)propanenitrile
69813-79-2

2-(4-tolyl)-2-(trimethylsiloxy)propanenitrile

Conditions
ConditionsYield
With MgAlCO3-HT In n-heptane for 0.0833333h; Ambient temperature;99%
With [(3,5-di-tert-Bu,2-OH)-C6H2-CH=N-CH2]2*Ti(O-i-Pr)4; N,N-dimethylaniline N-oxide In dichloromethane at 23℃; for 9h;99%
With C29H46LaN3Si2 at 15℃; for 1h; Inert atmosphere; Glovebox; Schlenk technique;99%
toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

para-methylacetophenone
122-00-9

para-methylacetophenone

1-(4-methylphenyl)-2-(p-tolylsulfonyloxy)ethanone
98475-04-8

1-(4-methylphenyl)-2-(p-tolylsulfonyloxy)ethanone

Conditions
ConditionsYield
With potassium peroxymonosulfate; 4-tolyl iodide In water; acetonitrile at 60℃; for 1h; Inert atmosphere;99%
With Dess-Martin periodane In acetonitrile for 3.5h; Reflux;92%
With [bis(acetoxy)iodo]benzene Microwave irradiation;85%

122-00-9Relevant articles and documents

Formal asymmetric hydration of non-activated alkenes in aqueous medium through a "chemoenzymatic catalytic system"

Schnapperelle, Ingo,Hummel, Werner,Groeger, Harald

, p. 1073 - 1076 (2012)

A direct one-pot conversion of (substituted) styrene(s) into the corresponding (substituted) (R)-phenylethan-1-ol(s) in a highly enantioselective manner has been achieved by using a "chemoenzymatic catalytic system", comprising a palladium-catalyzed Wacker-Tsuji oxidation and subsequent enantioselective enzymatic reduction of the in situ formed (substituted) acetophenone(s) (see scheme). Copyright

Structural effects on the β-scission reaction of alkoxyl radicals. Direct measurement of the absolute rate constants for ring opening of benzocycloalken-1-oxyl radicals

Bietti, Massimo,Lanzalunga, Osvaldo,Salamone, Michela

, p. 1417 - 1422 (2005)

(Chemical Equation Presented) The absolute rate constants for β-scission of a series of benzocycloalken-1-oxyl radicals and of the 2-(4-methylphenyl)-2-butoxyl radical have been measured directly by laser flash photolysis. The benzocycloalken-1-oxyl radicals undergo ring opening with rates which parallel the ring strain of the corresponding cycloalkanes. In the 1-X-indan-1-oxyl radical series, ring opening is observed when X = H, Me, whereas exclusive C-X bond cleavage occurs when X = Et. The factors governing the fragmentation regioselectivity are discussed.

Copper(I) Catalyzed Differential Peroxidation of Terminal and Internal Alkenes Using TBHP

Mir, Bilal Ahmad,Rajamanickam, Suresh,Begum, Pakiza,Patel, Bhisma K.

, p. 252 - 261 (2020)

Terminal and internal alkenes react contrarily with tert-butyl hydroperoxide (TBHP) giving various products. A Cu(I) catalyzed decarbonylative C–C bond formation followed by a carbonylation–peroxidation of vinyl arenes has been achieved using tert-butyl hydroperoxide (TBHP) as the oxidant in acetonitrile. Whereas, α-methyl styrenes yielded aryl methyl ketones and the α-substituted unsymmetrical internal alkenes afforded selective α-peroxidation under the identical reaction conditions. Concurrent peroxidation–carbonylation–cycloalkylation/cycloetherifiction of internal cyclic alkene such as indene is achieved by switching the solvent system from acetonitrile to cycloalkanes/cyclic ether. All these reactions proceed via radical paths generating interesting peroxo-compounds.

Continuous liquid phase acylation of toluene over HBEA zeolite: Solvent effects and origin of the deactivation

Chen, Zhihua,Chen, Wenqi,Tong, Tianxia,Zeng, Aiwu

, p. 231 - 238 (2014)

The continuous liquid phase Friedel-Crafts acylation of toluene (T) by acetic anhydride (AA) over HBEA zeolite was carried out in a fixed bed reactor, with acetic acid (AC) as a solvent. 4-Methylacetophenone (4-MAP) was selectively formed in the initial reaction stage. However, a rapid catalyst deactivation occurred with a sharp decrease of the conversion of acetic anhydride, and this was mainly caused by 4-MAP and heavy compounds ('coke') existing in the zeolite pore, which poisoned the active sites of the catalyst. The use of excess toluene and moderate acetic acid enhanced catalyst activity and stability to some extent as it limited both the retention of 4-MAP and the formation of 'coke'. Moreover, a considerable reduction of Broensted acid sites after deactivation revealed that the toluene acylation is primarily a Broensted acid catalyzed reaction.

PENTACOORDINATE ORGANOSILICATE AS AN ALKYLATING REAGENT: PALLADIUM CATALYZED METHYLATION OF ARYL HALIDES

Hatanaka, Yasou,Hiyama, Tamejiro

, p. 97 - 98 (1988)

Under the influence of palladium catalyst, tris(diethylamino)sulfonium difluorotrimethylsilicate is found to deliver the methyl group to aryl halides highly chemoselectively, and the corresponding methylated aromatic compounds are produced in moderate to high yields.

Nitrogen-doped carbon nanotubes encapsulate cobalt nanoparticles as efficient catalysts for aerobic and solvent-free selective oxidation of hydrocarbons

Lin, Xiu,Nie, Zhenzhen,Zhang, Liyun,Mei, Shuchuan,Chen, Yuan,Zhang, Bingsen,Zhu, Runliang,Liu, Zhigang

, p. 2164 - 2173 (2017)

The selective oxidation of hydrocarbons to the corresponding ketones with solvent-free and molecular oxygen as an oxidant is of great importance in academic and industrial fields in view of economy and environment. In this respect, we present the facile synthesis and characterization of excellent catalysts comprising cobalt nanoparticles encapsulated into graphitic nitrogen-doped carbon nanotubes (Co@GCNs) via one-pot pyrolysis of a chelate compound containing citric acid, melamine, and CoCl2·6H2O. The selective oxidation of ethylbenzene under molecular oxygen and solvent-free conditions is employed as a probe reaction to investigate the catalytic performance; the optimized catalyst shows the best conversion (68%) and selectivity for acetophenone (93%). Combination of the catalytic results of the control group and the different characterization methods demonstrates that high catalytic activity is due to the synergistic effect between metallic cobalt and nitrogen-doped carbon nanotubes. Moreover, the catalyst has high catalytic activity for the aerobic and solvent-free oxidation of other arylalkane substrates. The proposed mechanistic study illustrates that the reaction is a free radical reaction progressing through superoxide radical anions (?O2-).

-

Dermer et al.

, p. 2881 (1941)

-

Friedel-Crafts acylation of toluene using superacid catalysts in a solvent-free medium

El-Sharkawy,Al-Shihry, Shar S.

, p. 259 - 267 (2010)

Sulfated tin oxide and sulfated zirconia containing different amounts of sulfate and Al2O3-sulfated zirconia catalysts were prepared. The materials were characterized by DTA/TGA/DTG, XRD, FT-IR, and BET surface-area techniques. Surface acidity was determined using TGA of pyridine-pretreated samples, and acid strength was determined by potentiometric titration of the solid catalysts with n-butylamine in non-aqueous media. The catalytic activity of prepared samples was tested by Friedel-Crafts acylation of toluene with acetic acid anhydride. Incorporation of sulfate into SnO 2 impedes sintering and is associated with a decrease of surface area. Sulfated tin oxide has greater acidity and higher acid strength than Al3+-impregnated sulfated zirconia, giving, therefore, a higher yield of acylation products. Sulfated tin oxide was found to pass through maxima of higher acidity and higher efficiency for the acylation reaction when sulfate loading is 10 wt%. A good relationship between structural characteristics, acidity, and catalytic activity is observed.

Hierarchical zeolite Beta: An efficient and eco-friendly nanocatalyst for the Friedel-Crafts acylation of toluene

Selvin, Rosilda,Roselin, L. Selva,Khayyat, Suzan A.,Umar, Ahmad

, p. 4415 - 4420 (2013)

P-Methyacetophenone, the acylated product of toluene finds a wide range of applications in the flavors and fragrance industry. It is typically produced on an industrial scale by Friedel-Crafts acylation of toluene with acetic anhydride using homogeneous, corrosive and polluting acid catalysts such as aluminium chloride. The pollution problems related to this process such as the disposal of catalyst and treatment of acidic effluent needs to be replaced by a green process. The current work reports on the activity of hierarchical zeolite Beta in the liquid phase acylation of toluene with acetic anhydride. The liquid phase reactions were carried out in the temperature range of 60-140 °C in an autoclave. The effect of various reaction parameters such as time-on-stream (TOS), mole ratio of reactants, catalyst loading, and reaction temperature on the rates of reaction has been investigated. Under the optimum reaction conditions the performance of hierarchical zeolite Beta was compared with nanocrystalline zeolite Beta. It was found that hierarchical zeolite Beta catalyst exhibit higher activity, which is due to the hierarchical porosity and to the nano size of the Beta zeolite catalyst particles allows faster diffusion of the products out of the catalyst. Copyright

Efficient photodecarboxylation of 3- and 4-acetylphenylacetic acids in aqueous solution

Huck, Lawrence A.,Xu, Musheng,Forest, Kaya,Wan, Peter

, p. 1760 - 1768 (2004)

The photochemistry of 3- and 4-acetylphenylacetic acids (6 and 7) has been studied in aqueous solution. This work is a continuation of research efforts aimed at understanding the structural effects on the efficacy for benzyl carbanion photogeneration via photodecarboxylation. The nitro group (at the 3- and 4-positions) is known to be an exceptionally good activating group on the benzene ring - because of its enhanced electron-withdrawing effect in the excited triplet state - for photodecarboxylation and the related photo-retro-aldol type process. It is shown in this work that the acetyl group is an equally good activating group for the photodecarboxylation. Thus, the photochemistry of 6 and 7 parallels much of what was observed for the corresponding nitrophenylacetic acids 1 and 2. Both 6 and 7 photodecarboxylate efficiently (Φd = 0.60 and 0.22, respectively, at pH 7) via the carboxylate form, to give observable (by laser flash photolysis) benzyl carbanion or related intermediates. The meta isomer 6 displays an acid-catalyzed pathway for photodecarboxylation at pH 3 and along with its enhanced overall reactivity, is consistent with a meta effect of the acetyl group. Triplet state reactivity is inferred from sensitization and laser flash photolysis experiments. Based on the results of this work, the acetyl group may now be viewed as an "enhanced" electron-withdrawing group (in the excited state) when attached to a benzene ring (i.e., in acetophenone derivatives) that is capable of inducing ionic reactions, which is not the traditional photochemistry that is expected from such compounds.

Surface Coordination of Multiple Ligands Endows N-Heterocyclic Carbene-Stabilized Gold Nanoclusters with High Robustness and Surface Reactivity

Shen, Hui,Xu, Zhen,Hazer, Maryam Sabooni Asre,Wu, Qingyuan,Peng, Jian,Qin, Ruixuan,Malola, Sami,Teo, Boon K.,H?kkinen, Hannu,Zheng, Nanfeng

, p. 3752 - 3758 (2021)

Deciphering the molecular pictures of the multi-component and non-periodic organic-inorganic interlayer is a grand technical challenge. Here we show that the atomic arrangement of hybrid surface ligands on metal nanoparticles can be precisely quantified through comprehensive characterization of a novel gold cluster, Au44(iPr2-bimy)9(PA)6Br8 (1), which features three types of ligands, namely, carbene (1,3-diisopropylbenzimidazolin-2-ylidene, iPr2-bimy), alkynyl (phenylacetylide, PA), and halide (Br), respectively. The delicately balanced stereochemical effects and bonding capabilities of the three ligands give rise to peculiar geometrical and electronic structures. Remarkably, despite its complex and highly distorted surface structure, cluster 1 exhibits unusual catalytic properties and yet it is highly stable, both chemically and thermally. Moreover, rich reactive sites on the cluster surface raise the prospect of bio-compatibility (as it can be functionalized to yield water-soluble derivatives) and bio-applications.

-

Heine,Cottle,Van Mater

, p. 524 (1946)

-

NOVEL TYPES OF TRANSFORMATIONS OF α-AZIDOSTYRENE DERIVATIVES AND 3-ARYL-2H-AZIRINES IN THE PRESENCE OF HEXACARBONYLMOLYBDENUM

Nitta, Makoto,Kobayashi, Tomoshige

, p. 1715 - 1718 (1983)

The reaction of α-azidostyrene derivatives with hexacarbonylmolybdenum was found to give 2,5-diarylpyrroles and acetophenone derivatives via a complexed 1-arylvinylnitrene intermediate, while that of 3-aryl-2H-azirines gave 2,4-diarylpyrroles in addition to acetophenone derivatives and 2,5-diarylpyrazines.

An efficient oxidation of alcohols by aqueous H2O2 with 1,3-dibromo-5,5-dimethylhydantoin

Lee, Jieun,Lee, Jong Chan

, p. 895 - 898 (2018)

An efficient protocol is described for the oxidation of alcohols to the corresponding aldehydes or ketones with 1,3-dibromo-5,5-dimethylhydantoin in the presence of aqueous H2O2.

Palladium-catalyzed cross-methylation of haloarenes possessing active hydrogen atoms by intramolecularly stabilized dimethylindium and dimethylaluminum reagents

Jaber, Nimer,Gelman, Dmitri,Schumann, Herbert,Dechert, Sebastian,Blum, Jochanan

, p. 1628 - 1632 (2002)

While the intramolecularly stabilized aluminum complex [(CH3)2AlOCH2CH2 N(CH3)2]2 (2a) reacts readily with 4-bromophenol to give methane and [(4-BrC6H4O)su

Synthesis of ketones with alkyl phosphonates and nitriles as acyl cation equivalent: Application of dephosphonylation reaction of β-functionalized phosphonate with hydride

Jang, Won Bum,Shin, Won Suk,Hong, Jong Eun,Lee, Shi Yong,Oh, Dong Young

, p. 3333 - 3339 (1997)

The preparation of several α-substituted ketones is performed in a one-pot procedure with alkyl phosphonates and aromatic nitriles by subsequent treatment of LiAlH4. A new method for nitriles used as an acyl cation equivalent is described.

Nanocrystalline magnesium oxide-stabilized molybdenum: An efficient heterogeneous catalyst for the aerobic oxidation of alcohols to carbonyl compounds

Kantam, M. Lakshmi,Yadav, Jagjit,Laha, Soumi,Sreedhar, Bojja,Bhargava, Suresh

, p. 2575 - 2582 (2008)

A nanocrystalline magnesium oxide-stabilized molybdenum(VI) complex catalyzed the oxidation of primary and secondary alcohols to carbonyl compounds in excellent yields using molecular oxygen as stoichiometric oxidant. The nanomaterials with their three-dimensional structure and defined size and shape act as suitable supports for metal complexes. The catalyst can be reused for four runs without any significant loss of activity.

Friedel-crafts acylation reactions in pyridinium based ionic liquids

Xiao, Ying,Malhotra, Sanjay V.

, p. 3609 - 3613 (2005)

The Friedel-Crafts acylations of representative aromatic compounds with acetic anhydride in pyridinium based ionic liquids (ILs) were investigated. The effect of factors such as reactant composition, catalyst-IL composition, catalyst dosage and reaction temperature were studied. The reactions were found to proceed under relatively mild conditions with excellent conversions; and a simple product isolation procedure was achieved. ILs could also be recycled and reused effectively, thus rendering green characteristic to this reaction.

ESI-MS detection of proposed reaction intermediates in the air-promoted and ligand-modulated oxidative heck reaction

Enquist, Per-Anders,Nilsson, Peter,Sjoeberg, Per,Larhed, Mats

, p. 8779 - 8786 (2006)

Electrospray ionization mass spectrometry (ESI-MS) and subsequent MS/MS analyses were used to directly detect palladium-containing cationic reaction intermediates in a ligand controlled palladium(II)-catalyzed oxidative Heck arylation. All potential intermediates were observed as dmphen-ligated palladium(II) species, suggesting that the dmphen bidentate ligand is attached to the metal center during the entire catalytic cycle. The study supports previous mechanistic propositions and provides new information regarding the composition of aryl-containing Pd(II) complexes in an ongoing oxidative Heck reaction. In addition, sodium acetate was found to be a useful base alternative to previously used tertiary amines.

Temperature dependent solvent effects in photochemistry of 1-phenylpentan-1-ones

Klan, Petr,Literak, Jaromir

, p. 2007 - 2018 (1999)

Temperature dependent solvent effects have been investigated on the Norrish Type II reaction of 1-phenylpentan-1-one and its p-methyl derivative. Efficiencies of the photoreaction were studied in terms of solvent polarity and base addition as a function of temperature. Such a small structure change as the p-methyl substitution in 1-phenylpentan-1-one altered the temperature dependent photoreactivity in presence of weak bases. The experimental results suggest that the hydrogen bonding between the Type II biradical intermediate OH group and the solvent is weaker for 1-(4-methylphenyl)pentan-1-one than that for 1-phenylpentan-1-one at 20°C but the interactions probably vanish in both cases at 80°C.

-

Simons,Randall,Archer

, p. 1796 (1939)

-

Ester Cleavage in Superacid Media Involving Diprotonated Gitonic Carboxonium Dications

Olah, George A.,Hartz, Nikolai,Rasul, Golam,Burrichter, Arwed,Prakash, G. K. Surya

, p. 6421 - 6427 (1995)

The reactivity of protonated and methylated methyl ester in superacidic media was investigated by experiment and theory.Protonated methyl acetate was found to undergo slow acyl oxygen cleavage at -78 deg C in FSO3H/SbF5/SO2 solution to give acetyl cation and methyloxonium ion. 1,1-Dimethoxyethyl cation (methylated methyl acetate) was found to undergo slow methyl exchange in CD3SO3F/SbF5 solution.The reaction of 1,1-dimethoxyethyl cation with toluene in the presence of trifluoromethanesulfonic acid at -78 deg C gave acylation in 4percent yield.Theoretical calculations at the MP4(SDTQ)/6-31G*//MP2/6-31G* level of theory were performed to find stationary points on the potential energy surface of the mono- and diactivated ester system.Based on the available evidence a new mechanism for the acid-catalyzed ester cleavage in superacidic media is proposed.

-

Groggins,Nagel

, p. 1313,1314 (1934)

-

Synthesis of a 2,7-dioxatricyclo[4.2.1.03,8]nonane: A model study for possible application in a synthesis of dictyoxetane

Marshall,Mapp,Heathcock

, p. 9135 - 9145 (1996)

A method for the synthesis of the 2,7-dioxatricyclo[4.2.1.03,8]nonane ring system characteristic of the marine diterpene dictyoxetane has been developed. This method utilizes a dipolar cycloaddition of a 3-oxidopyrylium salt to create the carbon skeleton and employs an intramolecular S(N)2 displacement to form the oxetane ring. The route described could easily be adapted to incorporate additional functionality, making it potentially useful in a total synthesis of dictyoxetane.

Acylation of Toluene with Acetic Anhydride over Beta Zeolites: Influence of Reaction Conditions and Physicochemical Properties of the Catalyst

Botella,Corma,Lopez-Nieto,Valencia,Jacquot

, p. 161 - 168 (2000)

Acylation of toluene with acetic anhydride was carried out over Beta-type zeolites in a stainless steel autoclave. At low temperature, i.e., 150°C, and an arene/anhydride molar ratio 10-20, high yields of 4-methylacetophenone were obtained with selectivity close to 100%. The reaction is limited by the poisoning of the active sites by adsorption of the product and pore blockage due to coke -type products. Acid site accessibility is of paramount importance for this reaction, and the use of a nanocrystalline Beta zeolite as catalyst minimizes catalyst decay. This, combined with an optimum framework composition, allows the preparation of active and selective acylation catalysts based on Beta zeolite.

Visible light-mediated, high-efficiency oxidation of benzyl to acetophenone catalyzed by fluorescein

Geng, Haoxing,Liu, Xin,Zhu, Qing

supporting information, (2021/12/20)

An environmentally friendly aerobic oxidation of benzyl C(sp3)-H bonds to ketones via selective oxidation catalysis was developed. Fluorescein is an efficient photocatalyst with excellent chemical selectivity. The reaction has a wide substrate scope, and a successful gram-scale experiment demonstrated its potential industrial utility.

Selective Activation of Unstrained C(O)-C Bond in Ketone Suzuki-Miyaura Coupling Reaction Enabled by Hydride-Transfer Strategy

Zhong, Jing,Zhou, Wuxin,Yan, Xufei,Xia, Ying,Xiang, Haifeng,Zhou, Xiangge

supporting information, p. 1372 - 1377 (2022/02/23)

A Rh(I)-catalyzed ketone Suzuki-Miyaura coupling reaction of benzylacetone with arylboronic acid is developed. Selective C(O)-C bond activation, which employs aminopyridine as a temporary directing group and ethyl vinyl ketone as a hydride acceptor, occurs on the alkyl chain containing a β-position hydrogen. A series of acetophenone products were obtained in yields up to 75%.

Electrochemical Aerobic Oxidative Cleavage of (sp3)C-C(sp3)/H Bonds in Alkylarenes

Liu, Shuai,Liu, Zhong-Quan,Shen, Tong,Shen, Xu,Wang, Nengyong,Wu, Jintao,Yang, Le,Zhao, Jianyou

, p. 3286 - 3295 (2022/03/14)

An electrochemistry-promoted oxidative cleavage of (sp3)C-C(sp3)/H bonds in alkylarenes was developed. Various aryl alkanes can be smoothly converted into ketones/aldehydes under aerobic conditions using a user-friendly undivided cell setup. The features of air as oxidant, scalability, and mild conditions make them attractive in synthetic organic chemistry.

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