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  • 2'-Hydroxyacetophenone CAS 118-93-4 o-Hydroxyacetophenone CAS no 118-93-4 1-(2-Hydroxyphenyl)ethanone

    Cas No: 118-93-4

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118-93-4 Usage

Description

It is a typical flavour additive for cherry kernel, cinnamon, rum, tobacco, coumarin, and tropical fruit. Moreover, it can be used as the intermediate or raw material in organic synthesis. Specifically, this chemical may act as the raw material to prepare a Schiff’s base al-alkoxide initiator that facilitates the controlled polymerization of DL-lactide.1 This substance can also function as the effective component in balsamic compounds for fabricating taste modifying compositions.2 Additionally, this chemical has been employed to react with benzoyl chloride for generating 2-(2-Amino-3-methoxyphenyl)-4-oxo-4H-[1]benzopyran, which exhibits good performance for treating cancer and other proliferative diseases such as psoriasis and restenosis.3

Reference

Bhaw-Luximon, A.; Jhurry, D.; Spassky, N., Controlled polymerization of DL-lactide using a Schiff's base al-alkoxide initiator derived from 2-hydroxyacetophenone. Polym. Bull. 2000, 44, 31-38. Johann Wonschick; Clemens M. Putter; Keepe, E., TASTE MODIFYING COMPOSITIONS PCT WO 2016/103183 A1 2016. Alexander J Bridges; Saltiel, A. R., 2-(2-Amino-3-methoxyphenyl)-4-oxo-4H-[1]benzopyran for treating proliferative disorders US Patent US5525625 1996.

Chemical Properties

Different sources of media describe the Chemical Properties of 118-93-4 differently. You can refer to the following data:
1. clear yellow to brown liquid
2. 2-Hydroxyacetophenone has a sweet, heavy floral, herbaceous odor, reminiscent of mown hay or hawthorn

Occurrence

Reported found in beef, cassia oil, cocoa, cocoa powder, coffee, Jamaican rum, tomato, Scotch whiskey, sherry, tea, mountain papaya, papaya, roasted almond and black choke berry

Uses

Different sources of media describe the Uses of 118-93-4 differently. You can refer to the following data:
1. 2'-Hydroxyacetophenone is used as pharmaceutical intermediate.
2. 2’Hydroxyacetophenone is a phenolic compound used in the synthesis of potential anti-myobacterial and anticancer agents.

Preparation

Preparation by Fries rearrangement of phenyl acetate, with Lewis acidsaluminium chloride.

Aroma threshold values

Detection: 5.5 ppm; aroma characteristics at 2.0%: phenolic, sharp, benzaldehyde, cherry pit, tropical, melon with a tobacco afternote

Taste threshold values

Taste characteristics at 5.0 ppm: naphthyl, cinnamon, cherry pit, coumarin, phenolic, tobacco and honey.

Synthesis Reference(s)

Tetrahedron Letters, 24, p. 377, 1983 DOI: 10.1016/S0040-4039(00)81412-4

General Description

Pharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards

Check Digit Verification of cas no

The CAS Registry Mumber 118-93-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 8 respectively; the second part has 2 digits, 9 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 118-93:
(5*1)+(4*1)+(3*8)+(2*9)+(1*3)=54
54 % 10 = 4
So 118-93-4 is a valid CAS Registry Number.

118-93-4SDS

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 2'-Hydroxyacetophenone

1.2 Other means of identification

Product number -
Other names 2‘-Hydroxyacetophenone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
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:118-93-4 SDS

118-93-4Synthetic route

O-Ethoxycarbonyl-o-acetylphenol
64042-56-4

O-Ethoxycarbonyl-o-acetylphenol

o-hydroxyacetophenone
118-93-4

o-hydroxyacetophenone

Conditions
ConditionsYield
With sodium hydrogen telluride In ethanol for 0.5h; Quantum yield; Heating; buffer: deoxygen. acetic acid;100%
1-(2-((3-methylbut-2-en-1-yl)oxy)phenyl)ethanone
70538-46-4

1-(2-((3-methylbut-2-en-1-yl)oxy)phenyl)ethanone

o-hydroxyacetophenone
118-93-4

o-hydroxyacetophenone

Conditions
ConditionsYield
With titanium tetrachloride; tetra-(n-butyl)ammonium iodide In dichloromethane at -78℃; for 0.5h; deprenylation;100%
acide chromone carboxylique-2
4940-39-0

acide chromone carboxylique-2

ethylenediamine
107-15-3

ethylenediamine

A

o-hydroxyacetophenone
118-93-4

o-hydroxyacetophenone

B

5-(o-hydroxyphenyl)-2,3-dihydro-1,4-diazepine-7-carboxylic acid
89221-22-7

5-(o-hydroxyphenyl)-2,3-dihydro-1,4-diazepine-7-carboxylic acid

Conditions
ConditionsYield
In pyridine; methanol at 50℃; for 408h;A n/a
B 99.1%
o-acetoxyacetophenone
7250-94-4

o-acetoxyacetophenone

o-hydroxyacetophenone
118-93-4

o-hydroxyacetophenone

Conditions
ConditionsYield
With β‐cyclodextrin In water at 60℃; for 0.133333h; Microwave irradiation;99%
With ytterbium(III) chloride In neat (no solvent) at 70 - 120℃; for 0.0333333h; Microwave irradiation; Green chemistry;98%
With β‐cyclodextrin In water; acetone at 60℃; for 5h; Green chemistry;93%
With sodium perborate In methanol at 25℃; for 0.25h;82%
1-(2-ethoxyphenyl)ethanone
2142-67-8

1-(2-ethoxyphenyl)ethanone

o-hydroxyacetophenone
118-93-4

o-hydroxyacetophenone

Conditions
ConditionsYield
With 1-n-butyl-3-methylimidazolim bromide at 200 - 220℃; for 0.5h; Microwave irradiation; Inert atmosphere;99%
1-(2-(tetrahydro-2H-pyran-2-yloxy)phenyl)ethanone
204703-70-8

1-(2-(tetrahydro-2H-pyran-2-yloxy)phenyl)ethanone

o-hydroxyacetophenone
118-93-4

o-hydroxyacetophenone

Conditions
ConditionsYield
With β‐cyclodextrin In water at 60℃; for 0.133333h; Microwave irradiation;98%
With β‐cyclodextrin In water; acetone at 60℃; for 5h; Green chemistry;95%
With ytterbium(III) chloride In neat (no solvent) at 70 - 120℃; for 0.0333333h; Microwave irradiation; Green chemistry;93%
4CH3(1-)*Zn(2+)*Li(1+)

4CH3(1-)*Zn(2+)*Li(1+)

salicylic acid
69-72-7

salicylic acid

o-hydroxyacetophenone
118-93-4

o-hydroxyacetophenone

Conditions
ConditionsYield
Stage #1: 4CH3(1-)*Zn(2+)*Li(1+); salicylic acid In tetrahydrofuran; diethyl ether; hexane at 20℃; Schlenk technique; Inert atmosphere;
Stage #2: With iodine In tetrahydrofuran; diethyl ether; hexane at 20℃; Solvent; Schlenk technique; Inert atmosphere; chemoselective reaction;
97%
1-[2-(methoxymethoxy)phenyl]ethanone
6515-18-0

1-[2-(methoxymethoxy)phenyl]ethanone

o-hydroxyacetophenone
118-93-4

o-hydroxyacetophenone

Conditions
ConditionsYield
With β‐cyclodextrin In water at 60℃; for 0.133333h; Microwave irradiation;97%
With ytterbium(III) chloride In neat (no solvent) at 70 - 120℃; for 0.0333333h; Microwave irradiation; Green chemistry;92%
With β‐cyclodextrin In water; acetone at 60℃; for 5h; Green chemistry;90%
2-Methoxyacetophenone
579-74-8

2-Methoxyacetophenone

o-hydroxyacetophenone
118-93-4

o-hydroxyacetophenone

Conditions
ConditionsYield
With aluminum (III) chloride In dichloromethane at -5 - 25℃;96%
With hydrogen iodide at 25℃; for 24h; Inert atmosphere;89%
With 1-n-butyl-3-methylimidazolim bromide at 220℃; for 0.666667h; Inert atmosphere; Microwave irradiation;85%
2-(1-hydroxyethyl)phenol
87804-23-7, 62019-23-2

2-(1-hydroxyethyl)phenol

o-hydroxyacetophenone
118-93-4

o-hydroxyacetophenone

Conditions
ConditionsYield
With bismuth (III) nitrate pentahydrate; cellulose supported copper(0); oxygen In acetonitrile at 60℃; for 0.5h;96%
With dihydrogen peroxide In water; acetonitrile at 25℃; for 1.25h;95%
With manganese(III) Schiff-base; dihydrogen peroxide at 20℃; for 4.5h;93%
3-allylacetylacetone
10151-22-1

3-allylacetylacetone

o-hydroxyacetophenone
118-93-4

o-hydroxyacetophenone

Conditions
ConditionsYield
With potassium acetate; copper diacetate; manganese triacetate In acetic acid at 50℃; for 0.333333h;96%
Stage #1: 3-allylacetylacetone With hydrogenchloride; palladium chloride*2MeCN; copper dichloride In 1,4-dioxane; water at 70℃; for 15h;
Stage #2: With chloranil at 100℃; for 18h;
51%
Multi-step reaction with 2 steps
1: hydrogenchloride; copper dichloride; palladium chloride*2MeCN / 1,4-dioxane; water / 15 h / 70 °C
2: palladium chloride*2MeCN; chloranil / 1,4-dioxane / 18 h / 100 °C
View Scheme
Phenyl acetate
122-79-2

Phenyl acetate

o-hydroxyacetophenone
118-93-4

o-hydroxyacetophenone

Conditions
ConditionsYield
for 0.116667h; Rearrangement; microwave irradiation;95%
With aluminum (III) chloride In neat (no solvent) at 140 - 150℃; Fries Phenol Ester Rearrangement;90%
With hydrogen fluoride supported on silica gel In neat (no solvent) at 55℃; for 4h; Temperature; Green chemistry;77%
2-hydroxyacetophenoneoxime
1196-29-8

2-hydroxyacetophenoneoxime

o-hydroxyacetophenone
118-93-4

o-hydroxyacetophenone

Conditions
ConditionsYield
With periodic acid at 20℃; for 0.0666667h;95%
With Iron(III) nitrate nonahydrate; oxygen In toluene at 37℃; under 760.051 Torr; for 1.5h; Schlenk technique; Green chemistry;94%
With phosphoric acid In water at 95℃; for 4h;92%
2,4-dinitrophenylhydrazone of 2'-hydroxyacetophenone
17744-50-2

2,4-dinitrophenylhydrazone of 2'-hydroxyacetophenone

o-hydroxyacetophenone
118-93-4

o-hydroxyacetophenone

Conditions
ConditionsYield
With aluminum oxide; HMTAB for 0.05h; microwave irradiation;95%
1-{2-[(triisopropylsilyl)oxy]phenyl}ethanone

1-{2-[(triisopropylsilyl)oxy]phenyl}ethanone

o-hydroxyacetophenone
118-93-4

o-hydroxyacetophenone

Conditions
ConditionsYield
With potassium acetate In water; N,N-dimethyl-formamide at 25℃; for 11h;95%
1-(2-benzenesulfonyloxy-phenyl)-ethanone
106276-56-6

1-(2-benzenesulfonyloxy-phenyl)-ethanone

o-hydroxyacetophenone
118-93-4

o-hydroxyacetophenone

Conditions
ConditionsYield
With potassium hydroxide In toluene; tert-butyl alcohol at 100℃; for 0.5h; Inert atmosphere;95%
o-Hydroxyethylbenzene
90-00-6

o-Hydroxyethylbenzene

o-hydroxyacetophenone
118-93-4

o-hydroxyacetophenone

Conditions
ConditionsYield
With oxygen In water at 25℃; for 2.2h;94%
With cerium(III) chloride In water at 25℃; for 24h; Irradiation; Green chemistry;50%
5-chloro-2-hydroxyacetophenone
1450-74-4

5-chloro-2-hydroxyacetophenone

o-hydroxyacetophenone
118-93-4

o-hydroxyacetophenone

Conditions
ConditionsYield
With 1.5mol% Pd/C; hydrogen; sodium hydrogencarbonate In methanol at 20℃; for 0.833333h; regioselective reaction;93%
With ethanol; palladium on activated charcoal; sodium acetate Hydrogenation;
1-(2-(((1,1-dimethylethyl)dimethylsilyl)oxy)phenyl)ethanone
120820-40-8

1-(2-(((1,1-dimethylethyl)dimethylsilyl)oxy)phenyl)ethanone

o-hydroxyacetophenone
118-93-4

o-hydroxyacetophenone

Conditions
ConditionsYield
With potassium-exchanged zirconium hydrogen phosphate In water; acetone at 60℃; for 4h; desilylation;93%
With lithium acetate In water; N,N-dimethyl-formamide at 25℃; for 4h; Inert atmosphere;91%
With water; 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 20℃; for 0.0833333h; chemoselective reaction;91%
1-(2-hydroxyphenyl)ethan-1-one O-methyl oxime
54758-74-6

1-(2-hydroxyphenyl)ethan-1-one O-methyl oxime

o-hydroxyacetophenone
118-93-4

o-hydroxyacetophenone

Conditions
ConditionsYield
With hydrogenchloride In diethyl ether92%
With hydrogenchloride In diethyl ether at 20℃;87%
With water In acetonitrile for 0.75h; Quantum yield; Irradiation;
2'-allyloxyacetophenone
53327-14-3

2'-allyloxyacetophenone

o-hydroxyacetophenone
118-93-4

o-hydroxyacetophenone

Conditions
ConditionsYield
With iodine at 20℃;92%
With chloro-trimethyl-silane; sodium iodide In acetonitrile for 0.0833333h;90%
Stage #1: 2'-allyloxyacetophenone With C12H37NiP4(1+)*C2F6NO4S2(1-) In tetrahydrofuran at 20℃; for 0.5h; Glovebox; Schlenk technique; Inert atmosphere;
Stage #2: With toluene-4-sulfonic acid In tetrahydrofuran for 15h; Glovebox; Schlenk technique; Reflux; Inert atmosphere;
87%
N,N-diethylsalicylamide
19311-91-2

N,N-diethylsalicylamide

chloromethyldiphenylsilane
144-79-6

chloromethyldiphenylsilane

o-hydroxyacetophenone
118-93-4

o-hydroxyacetophenone

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran at 0 - 20℃; for 0.5h; Inert atmosphere;92%
2-iodoacetophenone
2142-70-3

2-iodoacetophenone

o-hydroxyacetophenone
118-93-4

o-hydroxyacetophenone

Conditions
ConditionsYield
With copper(I) oxide; water; potassium carbonate; Sucrose at 140℃; for 18h; Sealed tube; Inert atmosphere;91%
With copper(l) iodide; triethanolamine; tetrabutylammomium bromide; water; potassium hydroxide at 120℃; for 24h; Inert atmosphere;86%
With copper(l) iodide; triethanolamine; tetrabutylammomium bromide; potassium hydroxide In water at 120℃; for 24h; Inert atmosphere; Sealed tube; Green chemistry;86%
With copper(I) oxide; caesium carbonate; toluene-4-sulfonic acid In water at 120℃; for 24h; Sealed tube;70%
2-acetylphenyl 4-methylbenzenesulfonate
70188-11-3

2-acetylphenyl 4-methylbenzenesulfonate

o-hydroxyacetophenone
118-93-4

o-hydroxyacetophenone

Conditions
ConditionsYield
With ytterbium(III) chloride In neat (no solvent) at 70 - 120℃; for 0.0333333h; Microwave irradiation; Green chemistry;91%
With β‐cyclodextrin In water at 60℃; for 0.133333h; Microwave irradiation;61%
With β‐cyclodextrin In water; acetone at 60℃; for 6h; Green chemistry;60%
2'-(propargyloxy)acetophenone
41580-73-8

2'-(propargyloxy)acetophenone

o-hydroxyacetophenone
118-93-4

o-hydroxyacetophenone

Conditions
ConditionsYield
tris(2,2'-bipyridine)nickel(II) tetrafluoroborate In N,N-dimethyl-formamide Ambient temperature; electrolysis;90%
2-hydroxyacetophenone phenylhydrazone
7327-78-8

2-hydroxyacetophenone phenylhydrazone

o-hydroxyacetophenone
118-93-4

o-hydroxyacetophenone

Conditions
ConditionsYield
With caro's acid; silica gel In dichloromethane for 2.5h; Heating;90%
acetic acid
64-19-7

acetic acid

phenol
108-95-2

phenol

o-hydroxyacetophenone
118-93-4

o-hydroxyacetophenone

Conditions
ConditionsYield
With boron trifluoride diethyl etherate for 0.05h; microwave irradiation;90%
With iron(III) chloride for 0.05h; Friedel Crafts acylation; Microwave irradiation; regioselective reaction;70%
1-(2-((4-methoxybenzyl)oxy)phenyl)ethanone
371258-91-2

1-(2-((4-methoxybenzyl)oxy)phenyl)ethanone

o-hydroxyacetophenone
118-93-4

o-hydroxyacetophenone

Conditions
ConditionsYield
With trichlorophosphate In 1,2-dichloro-ethane at 20℃; for 0.5h;90%
2-hydroxyacetophenone semicarbazone
22107-30-8

2-hydroxyacetophenone semicarbazone

o-hydroxyacetophenone
118-93-4

o-hydroxyacetophenone

Conditions
ConditionsYield
With phosphoric acid In water at 95℃; for 4h;89%
With potassium permanganate at 20℃; for 0.933333h; Ionic liquid; chemoselective reaction;89%
With phosphoric acid for 0.0138889h; microwave irradiation;77%
With sodium bismuthate; silica gel for 0.0666667h; Hydrolysis; microwave irradiation, solid phase reaction;76%
pyridine
110-86-1

pyridine

o-hydroxyacetophenone
118-93-4

o-hydroxyacetophenone

N-(2-hydroxyphenacyl)pyridinium iodide
6323-86-0

N-(2-hydroxyphenacyl)pyridinium iodide

Conditions
ConditionsYield
With iodine at 140℃; for 3h;100%
With iodine at 140℃; for 3h;100%
With iodine at 140℃; for 3h;100%
o-hydroxyacetophenone
118-93-4

o-hydroxyacetophenone

benzyl chloride
100-44-7

benzyl chloride

2'-benzyloxyacetophenone
31165-67-0

2'-benzyloxyacetophenone

Conditions
ConditionsYield
With potassium carbonate In acetone for 12h; Heating;100%
With sodium hydroxide; tetrabutylammomium bromide In dichloromethane for 24h; Ambient temperature;95%
With potassium carbonate In N,N-dimethyl-formamide for 6h; Inert atmosphere; Reflux;95%
o-hydroxyacetophenone
118-93-4

o-hydroxyacetophenone

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

1-(2-hydroxyphenyl)-3-(4-methoxyphenyl)-2-propen-1-one
3327-24-0

1-(2-hydroxyphenyl)-3-(4-methoxyphenyl)-2-propen-1-one

Conditions
ConditionsYield
With potassium hydroxide In ethanol; water Claisen-Schmidt Condensation;100%
Stage #1: o-hydroxyacetophenone With sodium hydroxide In ethanol; water at 0 - 5℃;
Stage #2: 4-methoxy-benzaldehyde In ethanol; water
100%
With sodium hydroxide In ethanol at 20℃;95%
o-hydroxyacetophenone
118-93-4

o-hydroxyacetophenone

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

2'-hydroxy-4-dimethylaminochalcone
65786-13-2, 6342-97-8

2'-hydroxy-4-dimethylaminochalcone

Conditions
ConditionsYield
Stage #1: o-hydroxyacetophenone With sodium hydroxide In ethanol; water at 0 - 5℃;
Stage #2: 4-dimethylamino-benzaldehyde In ethanol; water
100%
With potassium hydroxide In ethanol at 25℃;85%
With potassium hydroxide In ethanol at 25℃;85%
o-hydroxyacetophenone
118-93-4

o-hydroxyacetophenone

5-Bromo-2-hydroxyacetophenone
1450-75-5

5-Bromo-2-hydroxyacetophenone

Conditions
ConditionsYield
With sulfuric acid; C18H16Br4N2O3V; dihydrogen peroxide; potassium bromide In methanol; water at 20℃; for 0.333333h; Catalytic behavior;100%
With perchloric acid; dihydrogen peroxide; potassium bromide In water at 20℃; for 3h;99%
With o-xylylene bis(triethylammonium tribromide) In acetonitrile at 20℃; for 0.116667h; regioselective reaction;90%
carbon monoxide
201230-82-2

carbon monoxide

o-hydroxyacetophenone
118-93-4

o-hydroxyacetophenone

4-hydroxy[1]benzopyran-2-one
1076-38-6

4-hydroxy[1]benzopyran-2-one

Conditions
ConditionsYield
With selenium; 1,5-Diazabicyclo[5.4.0]undec-5-ene In tetrahydrofuran at 90℃;100%
With selenium; 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 100℃; under 22800 Torr; for 30h;100%
With selenium; 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 100℃; under 22800 Torr; for 30h; Mechanism; carbonylation of alkyl aryl ketones with CO using stoichiometric amount of Se, variation of temperature and solvent;100%
With triethylamine In tetrahydrofuran at 80℃; under 7355.08 Torr; for 4h;95%
With nitrobenzene; 1,8-diazabicyclo[5.4.0]undec-7-ene; selenium In tetrahydrofuran at 90℃; under 22800 Torr; for 30h; Mechanism; catalytic carbonylation of alkyl aryl ketones with CO by Se in the presence of oxidizing agent;68%
o-hydroxyacetophenone
118-93-4

o-hydroxyacetophenone

benzaldehyde
100-52-7

benzaldehyde

1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one
1214-47-7

1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one

Conditions
ConditionsYield
With potassium hydroxide In ethanol; water Claisen-Schmidt Condensation;100%
Stage #1: o-hydroxyacetophenone With sodium hydroxide In ethanol; water at 0 - 5℃;
Stage #2: benzaldehyde In ethanol; water
100%
With sodium hydroxide In ethanol at 20℃;96%
o-hydroxyacetophenone
118-93-4

o-hydroxyacetophenone

4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

2',4-dihydroxychalcone
34000-31-2, 13323-66-5

2',4-dihydroxychalcone

Conditions
ConditionsYield
Stage #1: o-hydroxyacetophenone With sodium hydroxide In ethanol; water at 0 - 5℃;
Stage #2: 4-hydroxy-benzaldehyde In ethanol; water
100%
With potassium hydroxide In ethanol at 25℃;85%
With potassium hydroxide In ethanol at 25℃;85%
o-hydroxyacetophenone
118-93-4

o-hydroxyacetophenone

chloromethyl methyl ether
107-30-2

chloromethyl methyl ether

1-[2-(methoxymethoxy)phenyl]ethanone
6515-18-0

1-[2-(methoxymethoxy)phenyl]ethanone

Conditions
ConditionsYield
Stage #1: o-hydroxyacetophenone With sodium hydride In tetrahydrofuran at 0℃; for 0.5h;
Stage #2: chloromethyl methyl ether In tetrahydrofuran at 0 - 20℃; for 1h;
100%
Stage #1: o-hydroxyacetophenone With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h;
Stage #2: chloromethyl methyl ether In tetrahydrofuran; mineral oil at 20℃; for 16h;
100%
Stage #1: o-hydroxyacetophenone With sodium hydride In tetrahydrofuran; paraffin oil at -10℃; for 0.5h;
Stage #2: chloromethyl methyl ether In tetrahydrofuran; paraffin oil for 1h;
80%
o-hydroxyacetophenone
118-93-4

o-hydroxyacetophenone

α,α'-dibromo-o-xylene
91-13-4

α,α'-dibromo-o-xylene

1,2-bis(2-acetylphenoxymethyl)benzene
89579-24-8

1,2-bis(2-acetylphenoxymethyl)benzene

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide for 6h; Heating;100%
o-hydroxyacetophenone
118-93-4

o-hydroxyacetophenone

methylamine
74-89-5

methylamine

2-(1-(methylimino)ethyl)phenol
875-54-7

2-(1-(methylimino)ethyl)phenol

Conditions
ConditionsYield
at 20℃; for 20h; Neat (no solvent);100%
In ethanol at 50℃; for 5h;100%
In ethanol at 50℃; for 5h;100%
In benzene for 2h; Heating;90%
o-hydroxyacetophenone
118-93-4

o-hydroxyacetophenone

cyanomethyl bromide
590-17-0

cyanomethyl bromide

2-(2-acetylphenoxy)acetonitrile
58430-35-6

2-(2-acetylphenoxy)acetonitrile

Conditions
ConditionsYield
With potassium carbonate In acetone at 50℃; for 96h;100%
With potassium phosphate In dimethyl sulfoxide at 60℃;93%
o-hydroxyacetophenone
118-93-4

o-hydroxyacetophenone

2-(2-bromoacetyl)hydroxybenzene
2491-36-3

2-(2-bromoacetyl)hydroxybenzene

Conditions
ConditionsYield
With copper(ll) bromide In chloroform Reflux;100%
With copper(ll) bromide In chloroform; ethyl acetate Heating;96%
With copper(ll) bromide In chloroform; ethyl acetate for 5h; Reflux;94%

118-93-4Relevant articles and documents

Nickel Hydride Catalyzed Cleavage of Allyl Ethers Induced by Isomerization

Kathe, Prasad M.,Berkefeld, Andreas,Fleischer, Ivana

supporting information, p. 1629 - 1632 (2021/02/09)

This report discloses the deallylation of O - and N -allyl functional groups by using a combination of a Ni-H precatalyst and excess Bronsted acid. Key steps are the isomerization of the O - or N -allyl group through Ni-catalyzed double-bond migration followed by Bronsted acid induced O/N-C bond hydrolysis. A variety of functional groups are tolerated in this protocol, highlighting its synthetic value.

Catalyst- and acid-free Markovnikov hydration of alkynes in a sustainable H2O/ethyl lactate system

Dandia, Anshu,Saini, Pratibha,Chithra,Vennapusa, Sivaranjana Reddy,Parewa, Vijay

, (2021/03/15)

An efficient and sustainable protocol for the hydration of alkynes has been developed under metal/acid/catalyst/ligand-free conditions in a water/ethyl lactate mixture. The hydrogen-bond network in the ethyl lactate and water mixture plays a crucial and decisive role in activating the alkynes for hydration to afford the corresponding methyl ketones. This strategy gives the Markovnikov (ketone) addition product selectively over other possible products. The essential role of hydrogen bonding has been confirmed by experimental and theoretical techniques. A probable mechanism has been suggested by various control tests. The efficacy of the method has been further explored for the competent production of value-added α,β-unsaturated carbonyl compounds through the reaction of aldehydes with alkynes as ketonic surrogates. The environmentally benign hydration method takes place under mild conditions, has broad functional-group compatibility, and uses the ethyl lactate/water (1:3) medium as a “green alternative” in the absence of any hazardous, harmful, or expensive substances.

Preparation method of O-methoxyacetophenone

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, (2021/02/10)

The invention relates to a preparation method of o-methoxyacetophenone. A composite catalyst containing heteropolyacid and Lewis acid is adopted and can effectively catalyze the reaction of dimethyl ether and o-hydroxyacetophenone so that the use of dimethyl sulfate and other highly toxic substances as reaction reagents is avoided, the production cost is lowered, the discharge of highly toxic substances is reduced, and the process is enabled to be greener and more environment-friendly.

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