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538-86-3 Usage

Chemical Properties

CLEAR COLOURLESS TO SLIGHTLY YELLOWISH LIQUID

Uses

Benzyl methyl ether is used to produce benzaldehyde. It is used as perfuming agents.

Synthesis Reference(s)

Canadian Journal of Chemistry, 54, p. 685, 1976 DOI: 10.1139/v76-099Chemistry Letters, 13, p. 1225, 1984Tetrahedron Letters, 20, p. 4679, 1979

Check Digit Verification of cas no

The CAS Registry Mumber 538-86-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,3 and 8 respectively; the second part has 2 digits, 8 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 538-86:
(5*5)+(4*3)+(3*8)+(2*8)+(1*6)=83
83 % 10 = 3
So 538-86-3 is a valid CAS Registry Number.
InChI:InChI=1/C8H10O/c1-9-7-8-5-3-2-4-6-8/h2-6H,7H2,1H3

538-86-3 Well-known Company Product Price

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  • Alfa Aesar

  • (B23490)  Benzyl methyl ether, 97%   

  • 538-86-3

  • 10g

  • 402.0CNY

  • Detail
  • Alfa Aesar

  • (B23490)  Benzyl methyl ether, 97%   

  • 538-86-3

  • 50g

  • 1129.0CNY

  • Detail
  • Alfa Aesar

  • (B23490)  Benzyl methyl ether, 97%   

  • 538-86-3

  • 250g

  • 4051.0CNY

  • Detail

538-86-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Benzyl methyl ether

1.2 Other means of identification

Product number -
Other names Benzene, (methoxymethyl)-

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:538-86-3 SDS

538-86-3Synthetic route

2,6-di-tert-butyl-4-methylpyridine
38222-83-2

2,6-di-tert-butyl-4-methylpyridine

methyltriphenylbismuthonium tetrafluoroborate
278172-59-1

methyltriphenylbismuthonium tetrafluoroborate

benzyl alcohol
100-51-6

benzyl alcohol

A

benzyl methyl ether
538-86-3

benzyl methyl ether

B

2,6-di-tert-butyl-4-methylpyridinium tetrafluoroborate
160142-36-9

2,6-di-tert-butyl-4-methylpyridinium tetrafluoroborate

C

triphenylbismuthane
603-33-8

triphenylbismuthane

Conditions
ConditionsYield
In chloroform-d1 Kinetics; alcohol was added to mixt. (Ph3BiMe)(BF4) and 2,6-di-tert-butyl-4-methylpyridine in CDCl3 and allowed to react at 23°C for 4-7 h; detn. by NMR;A 95%
B 100%
C 100%
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

benzyl methyl ether
538-86-3

benzyl methyl ether

Conditions
ConditionsYield
With 1,1,3,3-Tetramethyldisiloxane; copper(II) bis(trifluoromethanesulfonate) In dichloromethane at 20℃;99%
With trimethylsilan; trimethylsilyl trifluoromethanesulfonate In dichloromethane 0 deg C, 30 min. then 28 deg C, 13 h.;96%
With triethylsilane; Nafion-H (perfluororesinsulfonic acid) In dichloromethane for 2h; Heating;96%
Benzyl acetate
140-11-4

Benzyl acetate

methyl iodide
74-88-4

methyl iodide

benzyl methyl ether
538-86-3

benzyl methyl ether

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide 1.) 0 deg C, 1 h, 2.) 25 deg C, 24 h;99%
dimethyl sulfate
77-78-1

dimethyl sulfate

benzyl alcohol
100-51-6

benzyl alcohol

benzyl methyl ether
538-86-3

benzyl methyl ether

Conditions
ConditionsYield
Stage #1: benzyl alcohol With potassium carbonate In acetone for 0.25h;
Stage #2: dimethyl sulfate In acetone for 15h; Reflux;
97%
With sodium hydroxide; zirconium (benzyldiethylammoniomethylphosphonate chloride) phosphate In ethanol; water; Petroleum ether at 42℃; for 8h;80.1%
With sodium hydroxide at 40℃;
methanol
67-56-1

methanol

carbon monoxide
201230-82-2

carbon monoxide

benzyl chloride
100-44-7

benzyl chloride

A

benzyl methyl ether
538-86-3

benzyl methyl ether

B

sodium phenylacetate
114-70-5

sodium phenylacetate

Conditions
ConditionsYield
With sodium hydroxide; dicobalt octacarbonyl at 60 - 65℃; under 760.051 - 2280.15 Torr;A n/a
B 97%
methanol
67-56-1

methanol

benzaldehyde
100-52-7

benzaldehyde

benzyl methyl ether
538-86-3

benzyl methyl ether

Conditions
ConditionsYield
With Decaborane at 20℃; for 22h; reductive etherification;96%
With phenyltellurotrimethylsilane; zinc(II) iodide In benzene for 3h; Ambient temperature;89 % Chromat.
methanol
67-56-1

methanol

benzyltributyltin
28493-54-1

benzyltributyltin

benzyl methyl ether
538-86-3

benzyl methyl ether

Conditions
ConditionsYield
With copper(II) bis(tetrafluoroborate) In acetonitrile for 1.5h; Irradiation;94%
benzyltributyltin
28493-54-1

benzyltributyltin

benzyl methyl ether
538-86-3

benzyl methyl ether

Conditions
ConditionsYield
With methanol; copper(II) bis(tetrafluoroborate) In acetonitrile Irradiation (UV/VIS); 1.5 h, λ > 200 nm;94%
methanol
67-56-1

methanol

benzyl alcohol
100-51-6

benzyl alcohol

A

benzyl methyl ether
538-86-3

benzyl methyl ether

B

dibenzyl ether
103-50-4

dibenzyl ether

Conditions
ConditionsYield
With copper(ll) bromide at 175℃; for 10h; Inert atmosphere; Sealed tube;A 93%
B 7%
With phosphoric acid at 350℃; under 36775.4 Torr;
With Cp*Ir(Cl)2(nBu2Im); silver trifluoromethanesulfonate at 110℃; for 12h;A 88 %Spectr.
B 6 %Spectr.
methanol
67-56-1

methanol

benzyl bromide
100-39-0

benzyl bromide

benzyl methyl ether
538-86-3

benzyl methyl ether

Conditions
ConditionsYield
With iron(II) sulfate at 75℃; for 12h;92%
Stage #1: methanol With potassium hydride In tetrahydrofuran at 25℃; for 8h; Metallation;
Stage #2: benzyl bromide In tetrahydrofuran Alkylation;
85%
With silver(II) oxide at 0℃;82%
methanol
67-56-1

methanol

benzyl alcohol
100-51-6

benzyl alcohol

benzyl methyl ether
538-86-3

benzyl methyl ether

Conditions
ConditionsYield
With bismuth(III) bromide In tetrachloromethane at 25℃; for 8h; Etherification;92%
Stage #1: methanol With 15-crown-5; potassium In tetrahydrofuran at 25℃;
Stage #2: benzyl alcohol In tetrahydrofuran
25%
Stage #1: benzyl alcohol With titanium tetrachloride In chloroform at 20℃; for 0.0166667h; Molecular sieve;
Stage #2: methanol In chloroform for 72h; Reflux;
20%
benzyl alcohol
100-51-6

benzyl alcohol

trimethyl orthoformate
149-73-5

trimethyl orthoformate

benzyl methyl ether
538-86-3

benzyl methyl ether

Conditions
ConditionsYield
With iodine at 20℃; for 0.5h;92%
benzyl alcohol
100-51-6

benzyl alcohol

methyl iodide
74-88-4

methyl iodide

benzyl methyl ether
538-86-3

benzyl methyl ether

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 20℃; for 16h;91%
With sodium hydride; 1-n-butyl-2,3-dimethylimidazolium hexafluorophosphate at 25℃; for 2h; Williamson synthesis;91%
With iron(III) perchlorate at 20℃; for 1h; neat (no solvent);90%
benzyl methoxymethyl ether
31600-55-2

benzyl methoxymethyl ether

benzyl methyl ether
538-86-3

benzyl methyl ether

Conditions
ConditionsYield
With chloro-trimethyl-silane; zinc(II) tetrahydroborate In diethyl ether; dichloromethane at 25℃; for 40h;90%
Trimethyl orthoacetate
1445-45-0

Trimethyl orthoacetate

benzyl alcohol
100-51-6

benzyl alcohol

benzyl methyl ether
538-86-3

benzyl methyl ether

Conditions
ConditionsYield
With iodine at 20℃; for 0.583333h;90%
With Montmorillonite KSF for 12h; Ambient temperature;83%
methanol
67-56-1

methanol

dibenzyl ether
103-50-4

dibenzyl ether

benzyl methyl ether
538-86-3

benzyl methyl ether

Conditions
ConditionsYield
With iron(III) chloride at 146.84℃; for 6h; Reagent/catalyst;89.3%
methanol
67-56-1

methanol

benzyl chloride
100-44-7

benzyl chloride

benzyl methyl ether
538-86-3

benzyl methyl ether

Conditions
ConditionsYield
With silver(II) oxide Ambient temperature;89%
With benzyltrimethylammonium chloride for 0.0833333h; Heating; Irradiation;87%
With potassium hydroxide
benzyl chloride
100-44-7

benzyl chloride

A

benzyl methyl ether
538-86-3

benzyl methyl ether

B

phenylacetic acid
103-82-2

phenylacetic acid

Conditions
ConditionsYield
With sodium hydroxide; cobalt tetracarbonyl anion In methanol at 55℃; for 4h;A 10%
B 85%
6,7-diazatricyclo<3.2.2.02,4>nona-6,8-diene N-oxide
55563-80-9

6,7-diazatricyclo<3.2.2.02,4>nona-6,8-diene N-oxide

A

benzyl methyl ether
538-86-3

benzyl methyl ether

B

benzyl chloride
100-44-7

benzyl chloride

Conditions
ConditionsYield
With hydrogenchloride In methanol Mechanism; Ambient temperature;A n/a
B 85%
methanol
67-56-1

methanol

benzoic acid
65-85-0

benzoic acid

benzyl methyl ether
538-86-3

benzyl methyl ether

Conditions
ConditionsYield
With aluminium(III) triflate; tris(2,4-pentanedionato)ruthenium(III); hydrogen; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In toluene at 160℃; under 45603.1 Torr; for 24h; Autoclave;84%
Trimethyl orthoacetate
1445-45-0

Trimethyl orthoacetate

benzyl alcohol
100-51-6

benzyl alcohol

A

benzyl methyl ether
538-86-3

benzyl methyl ether

B

Benzyl acetate
140-11-4

Benzyl acetate

Conditions
ConditionsYield
Montmorillonite KSF at 20℃; for 12h;A 83%
B 4%
(dimethoxy)methylsilane
16881-77-9

(dimethoxy)methylsilane

benzaldehyde
100-52-7

benzaldehyde

benzyl methyl ether
538-86-3

benzyl methyl ether

Conditions
ConditionsYield
Stage #1: (dimethoxy)methylsilane; benzaldehyde With dicarbonyl(pentamethylcyclopentadienyl)(4-methoxyphenyl)iron In dichloromethane for 4h; Inert atmosphere; Irradiation; Schlenk technique;
Stage #2: With sodium hydroxide In methanol; water Schlenk technique; Inert atmosphere;
82%
aluminium benzyl alcoholate
2092-14-0

aluminium benzyl alcoholate

methyl iodide
74-88-4

methyl iodide

benzyl methyl ether
538-86-3

benzyl methyl ether

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 59 - 70℃; for 48h;80%
triethylsilane
617-86-7

triethylsilane

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

benzyl methyl ether
538-86-3

benzyl methyl ether

Conditions
ConditionsYield
With 2,4,6-triphenylpyrilium perchlorate In acetonitrile for 0.166667h; Irradiation;80%
methanol
67-56-1

methanol

toluene
108-88-3

toluene

A

benzyl methyl ether
538-86-3

benzyl methyl ether

B

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
With tetrachloromethane; bis(acetylacetonate)oxovanadium; triethylamine at 175℃; for 14h; Inert atmosphere; Autoclave;A 80%
B 10%
diisopropyl phosphine oxide

diisopropyl phosphine oxide

A

benzyl methyl ether
538-86-3

benzyl methyl ether

B

di-isopropylphosphine
20491-53-6

di-isopropylphosphine

Conditions
ConditionsYield
With lithium aluminium tetrahydride In diethyl ether for 1h; Heating; reduction failed;A 79%
B 61%
With lithium aluminium tetrahydride In diethyl ether for 1h; Reflux;A 79%
B 61%
methanol
67-56-1

methanol

(S)-2-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-3-(4-hydroxy-phenyl)-propionic acid
1050-28-8

(S)-2-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-3-(4-hydroxy-phenyl)-propionic acid

A

benzyl methyl ether
538-86-3

benzyl methyl ether

B

L-tyrosine
60-18-4

L-tyrosine

Conditions
ConditionsYield
With potassium hydroxide; [bis(acetoxy)iodo]benzene at 0 - 5℃; for 1.5h;A 78%
B n/a
bromobenzene
108-86-1

bromobenzene

chloromethyl methyl ether
107-30-2

chloromethyl methyl ether

benzyl methyl ether
538-86-3

benzyl methyl ether

Conditions
ConditionsYield
Stage #1: bromobenzene With n-butyllithium In tetrahydrofuran at -78℃; for 1h;
Stage #2: chloromethyl methyl ether In tetrahydrofuran at -78 - 0℃; for 2h;
76%
With diethyl ether; sodium
chloromethyl methyl ether
107-30-2

chloromethyl methyl ether

phenol
108-95-2

phenol

benzyl methyl ether
538-86-3

benzyl methyl ether

Conditions
ConditionsYield
Stage #1: phenol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.25h; Inert atmosphere; Schlenk technique;
Stage #2: chloromethyl methyl ether In tetrahydrofuran at 0 - 25℃; for 2h; Inert atmosphere; Schlenk technique;
76%
methanol
67-56-1

methanol

C13H18ClNO3
135765-55-8

C13H18ClNO3

A

benzyl methyl ether
538-86-3

benzyl methyl ether

B

3-nitroso-3-methylbutanoic acid methyl ester
49680-44-6

3-nitroso-3-methylbutanoic acid methyl ester

C

benzyl chloride
100-44-7

benzyl chloride

Conditions
ConditionsYield
With triethylamine 1.) -20 deg C, 6 h, 2.) 20 deg C, 1 h;A n/a
B 24%
C n/a
D 75%
benzyl methyl ether
538-86-3

benzyl methyl ether

benzoyl chloride
98-88-4

benzoyl chloride

benzoic acid methyl ester
93-58-3

benzoic acid methyl ester

Conditions
ConditionsYield
With iron In 1,2-dichloro-ethane at 80℃; for 7h; Schlenk technique; Inert atmosphere; regioselective reaction;99%
With molybdenum(V) chloride In 1,2-dichloro-ethane at 80℃; for 3h;82%
benzyl methyl ether
538-86-3

benzyl methyl ether

methylmagnesium bromide
75-16-1

methylmagnesium bromide

ethylbenzene
100-41-4

ethylbenzene

Conditions
ConditionsYield
1,1'-bis-(diphenylphosphino)ferrocene; [1,1'-bis(diphenylphosphino)ferrocene]nickel(II) chloride; potassium iodide In diethyl ether; toluene at 80℃; for 10h;99%
benzyl methyl ether
538-86-3

benzyl methyl ether

toluene
108-88-3

toluene

Conditions
ConditionsYield
With palladium dichloride In methanol at 40℃; for 12h; Inert atmosphere; Green chemistry; chemoselective reaction;99%
With methanol; toluene-4-sulfonic acid at 25℃; for 7.5h; Reagent/catalyst; Inert atmosphere; Sealed tube; UV-irradiation;95%
With samarium diiodide; water In tetrahydrofuran; decane at 20℃;
With diisobutylaluminium hydride; sodium t-butanolate; bis(1,5-cyclooctadiene)nickel(0); 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride In tetrahydrofuran at 80℃; for 16h; Product distribution / selectivity; Inert atmosphere;82 %Chromat.
terephthalonitrile
623-26-7

terephthalonitrile

benzyl methyl ether
538-86-3

benzyl methyl ether

4-(methoxy(phenyl)methyl)benzonitrile

4-(methoxy(phenyl)methyl)benzonitrile

Conditions
ConditionsYield
With fac-tris(2-(4,6-difluorophenyl)pyridinato,N,C(2'))iridium(III); N-[3,5-bis(trifluoromethyl)phenyl]-2,4,6-triisopropylbenzenesulfonamide; potassium carbonate In acetone at 40℃; for 24h; Sealed tube; Inert atmosphere; Irradiation;99%
With tris[2-phenylpyridinato-C2,N]iridium(III); dipotassium hydrogenphosphate; Octanal; Methyl thioglycolate In N,N-dimethyl acetamide at -78 - 23℃; for 12h; Reagent/catalyst; Solvent; Irradiation; Inert atmosphere;77%
With thiobenzoic acid; potassium phosphate In N,N-dimethyl acetamide at 20℃; for 6h; Irradiation;55%
benzyl methyl ether
538-86-3

benzyl methyl ether

A

methanol
67-56-1

methanol

B

toluene
108-88-3

toluene

Conditions
ConditionsYield
With hydrogen In n-heptane at 160℃; under 750.075 Torr; for 6h; Catalytic behavior; Temperature;A 93%
B 98%
benzyl methyl ether
538-86-3

benzyl methyl ether

(4-chlorphenyl)magnesium bromide
873-77-8

(4-chlorphenyl)magnesium bromide

1-chloro-4-(methoxy(phenyl)methyl)benzene
7364-23-0

1-chloro-4-(methoxy(phenyl)methyl)benzene

Conditions
ConditionsYield
Stage #1: benzyl methyl ether With 2,3-dicyano-5,6-dichloro-p-benzoquinone In chlorobenzene at 80℃; for 1.5h; Inert atmosphere;
Stage #2: (4-chlorphenyl)magnesium bromide In chlorobenzene at 0℃; for 3h; Inert atmosphere;
97%
benzyl methyl ether
538-86-3

benzyl methyl ether

benzoic acid methyl ester
93-58-3

benzoic acid methyl ester

Conditions
ConditionsYield
With N-hydroxyphthalimide; oxygen In acetonitrile at 80℃; for 12h;95%
With tert.-butylhydroperoxide; C45H52CuN4O3 In decane; acetonitrile at 70℃; for 18h;93%
With sodium periodate; ruthenium trichloride In tetrachloromethane; water; acetonitrile for 8h; Ambient temperature;89%
benzyl methyl ether
538-86-3

benzyl methyl ether

5-nitroindole
6146-52-7

5-nitroindole

3,3′-benzylidenebis(5-nitro-1H-indole)
1173883-99-2

3,3′-benzylidenebis(5-nitro-1H-indole)

Conditions
ConditionsYield
With di-tert-butyl peroxide; iron(II) chloride at 80℃; for 1h; Inert atmosphere;95%
benzyl methyl ether
538-86-3

benzyl methyl ether

4-flourophenylmagnesium bromide
352-13-6

4-flourophenylmagnesium bromide

1-fluoro-4-(methoxy(phenyl)methyl)benzene

1-fluoro-4-(methoxy(phenyl)methyl)benzene

Conditions
ConditionsYield
Stage #1: benzyl methyl ether With 2,3-dicyano-5,6-dichloro-p-benzoquinone In chlorobenzene at 80℃; for 1.5h; Inert atmosphere;
Stage #2: 4-flourophenylmagnesium bromide In chlorobenzene at 0℃; for 3h; Inert atmosphere;
94%
benzyl methyl ether
538-86-3

benzyl methyl ether

α-azidobenzyl methyl ether
127700-29-2

α-azidobenzyl methyl ether

Conditions
ConditionsYield
With iodine(I) azide In acetonitrile for 0.416667h; Heating;93%
With [bis(acetoxy)iodo]benzene; trimethylsilylazide In acetonitrile at 0 - 25℃;88%
With polystyrene supported diazidoiodate(I) In acetonitrile at 83℃; for 4h;68%
benzyl methyl ether
538-86-3

benzyl methyl ether

anthranilic acid amide
28144-70-9

anthranilic acid amide

2-phenyl-4(3H)-quinazolinone
1022-45-3

2-phenyl-4(3H)-quinazolinone

Conditions
ConditionsYield
With oxygen In dimethyl sulfoxide at 120℃; under 760.051 Torr; for 12h; Temperature; Solvent; Schlenk technique; Sealed tube; Green chemistry;92%
benzyl methyl ether
538-86-3

benzyl methyl ether

4-CF3C6H4CN
455-18-5

4-CF3C6H4CN

N-benzyl-4-trifluoromethylbenzamide

N-benzyl-4-trifluoromethylbenzamide

Conditions
ConditionsYield
With iron(III) perchlorate hydrate In neat (no solvent) at 100℃; for 2h; Ritter Amidation;92%
benzyl methyl ether
538-86-3

benzyl methyl ether

benzonitrile
100-47-0

benzonitrile

N-benzylbenzamide
1485-70-7

N-benzylbenzamide

Conditions
ConditionsYield
With iron(III) perchlorate hydrate In neat (no solvent) at 100℃; for 2h; Catalytic behavior; Reagent/catalyst; Temperature; Ritter Amidation;91%
With iron(III) chloride for 12h; Ritter reaction; Heating;22%
benzyl methyl ether
538-86-3

benzyl methyl ether

para-xylene
106-42-3

para-xylene

2-benzyl-1,4-dimethylbenzene
13540-50-6

2-benzyl-1,4-dimethylbenzene

Conditions
ConditionsYield
iron(III) chloride at 90℃; for 12h; Friedel-Crafts reaction;90%
benzyl methyl ether
538-86-3

benzyl methyl ether

4-nitrobenzonitrile
619-72-7

4-nitrobenzonitrile

4-nitro-N-benzylbenzamide
2585-26-4

4-nitro-N-benzylbenzamide

Conditions
ConditionsYield
With iron(III) perchlorate hydrate In neat (no solvent) at 100℃; for 2h; Ritter Amidation;90%

538-86-3Relevant articles and documents

The Isotope Effects in the Reactions of Phenylcarbene with Alcoholic Matrices

Tomioka, Hideo,Ozaki, Yasuji,Izawa, Yasuji

, p. 1239 - 1240 (1983)

Product analysis studies on the reaction of phenylcarbene in deuterated alcoholic matrices at 77 K revealed that isotope effect on O-H (D) insertion is very small while substantial isotope effect was observed for C-H (D) insertion.

Billups et al.

, p. 7878,7879 (1973)

New concept for the preparation of potassium sodides: The use of hexane as a non-polar solvent

Grobelny, Zbigniew,Stolarzewicz, Andrzej,Morejko-Buz, Barbara,Winiarski, Antoni

, p. 2147 - 2150 (2003)

NaK alloy in contact with 15-crown-5 hexane solution became potassium sodide K+(15-crown-5)2Na-. After the evaporation of hexane the crystalline solid product was analyzed by X-ray diffraction and the lattice parameters were calculated. The potassium sodide thus obtained could be easily dissolved in tetrahydrofuran. A deep blue solution containing sodium anions and complexed potassium cations was formed with a very low concentration of solvated electrons, i.e. of the order of 10-7M. Potassium anions were not detected in this case. A new crystalline potassium sodide K+(DCH-24-crown-8)2Na- was obtained using NaK alloy and dicyclohexano-24-crown-8 hexane solution.

Solvolysis of benzyl phenyl ether in high-temperature aqueous methanol solution under high-pressure carbon dioxide

Taniguchi, Kenkichi,Nanao, Hidetaka,Sato, Osamu,Yamaguchi, Aritomo,Shirai, Masayuki

, p. 1658 - 1664 (2021/03/09)

Alcoholysis of benzyl phenyl ether to various aromatic compounds was studied in high-temperature aqueous methanol solution under high-pressure carbon dioxide conditions. The products formed included benzyl methyl ether, benzyl alcohol, phenol and toluene. As high as 70.7 ± 0.2% yield of monocyclic aromatic hydrocarbon with 16.1 ± 0.3% yield of benzyl methyl ether was obtained by treating benzyl phenyl ether with an aqueous solution with 0.2 molar fraction of methanol, under 17.7 MPa carbon dioxide for 1 h at 573 K.

Oxoammonium-Mediated Allylsilane–Ether Coupling Reaction

Carlet, Federica,Bertarini, Greta,Broggini, Gianluigi,Pradal, Alexandre,Poli, Giovanni

supporting information, p. 2162 - 2168 (2021/04/02)

A new C(sp3)?H functionalization reaction consisting of the oxidative α-allylation of allyl- and benzyl- methyl ethers has been developed. The C?C coupling could be carried out under mild conditions thanks to the use of cheap and green oxoammonium salts. The scope of the reaction was studied over 27 examples, considering the nature of the substituents on the two coupling partners.

Regulating Aromatic Alcohols Distributions by Cofeeding Methanol with Ethanol over Cobalt-Hydroxyapatite Catalyst

He, Lei,Li, Wen-Cui,Lu, An-Hui,Wang, Qing-Nan,Weng, Xue-Fei,Zhou, Bai-Chuan

, (2020/03/24)

Aromatic alcohols, often used for the synthesis of plasticizers, coatings and pharmaceuticals, are currently produced from the oxidation of petroleum-derived aromatic hydrocarbons. Herein, we report a non-petroleum and environmentally friendly route for the production of aromatic alcohols: cofeeding methanol with ethanol over cobalt-hydroxyapatite catalyst, in which the distribution of aromatic alcohols products can be regulated by varying methanol pressure. Co species on hydroxyapatite can activate both methanol and ethanol to yield their corresponding aldehydes (formaldehyde and acetaldehyde). The followed cross- and self-condensations of aldehydes are catalyzed by hydroxyapatite to produce acrolein and 2-butenal, which are the key intermediates for the formation of aromatic oxygenates. The sequential cross-condensation and dehydrocyclization of acrolein and 2-butenal yield benzaldehyde, which is then hydrogenated to benzyl alcohol. The direct production of benzyl alcohol from methanol and ethanol could be regarded as a cutting-edge example, which ensures a promising route for sustainable aromatic alcohols production.

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