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93-51-6

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93-51-6 Usage

Description

2-Methoxy-4-methylphenol has a characteristic aromatic odor (sweet, spicy, slightly vanilla-like) and a somewhat bitter taste (vanilla-like). May be prepared by methylation of homopyrocatechin using dimethyl sulfate and alkali; also by hydrogenation of vanillin.

Chemical Properties

Different sources of media describe the Chemical Properties of 93-51-6 differently. You can refer to the following data:
1. 2-Methoxy-4-methylphenol has a characteristic aromatic odor (sweet, spicy, slightly vanilla-like) and a somewhat bitter taste (vanilla-like).
2. Clear colorless to slightly yellow liquid

Occurrence

Occurs in beechwood tar; also identified in the essential oils of ylang-ylang, jasmine and anise seeds; it is one of the active constituents of creosote. Reported found in Gruyere cheese, smoked fish, cured pork, beer, rum, bourbon whiskey, malt and Scotch whiskey, sherry, white and red wine, cocoa, coffee, tea, mushrooms, mango, pear brandy, malt, wort, dried bonito, Bourbon vanilla, cuttlefish and green maté.

Uses

Different sources of media describe the Uses of 93-51-6 differently. You can refer to the following data:
1. 2-Methoxy-4-methylphenol is used in preparation of renewable bis(cyanate) esters.
2. 2-Methoxy-4-methylphenol is used for blending baking and smoked food flavors.

Preparation

By methylation of homopyrocatechin using dimethyl sulfate and alkali; also by hydrogenation of vanillin.

Aroma threshold values

Detection: 90 ppb. Aroma characteristics at 1.0%: smoky, sweet, phenolic, vanilla, spicy clove with a floral carnation nuance.

Taste threshold values

Taste characteristics at 1.0 to 1.25 ppm: sweet phenolic, spice, vanilla, medicinal, clove-like, smoky, guaia col-like with a woody, phenolic nuance.

General Description

2-Methoxy-4-methylphenol is the major component of black-ripe table olive aroma. It is the major anti-inflammatory compound in bamboo vinegar. Kinetics of reaction of 2-methoxy-4-methylphenol with chlorine atoms was studied.

Biochem/physiol Actions

Odor at 1.0%

Check Digit Verification of cas no

The CAS Registry Mumber 93-51-6 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 3 respectively; the second part has 2 digits, 5 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 93-51:
(4*9)+(3*3)+(2*5)+(1*1)=56
56 % 10 = 6
So 93-51-6 is a valid CAS Registry Number.
InChI:InChI=1/C8H10O2/c1-6-5-7(10-2)3-4-8(6)9/h3-5,9H,1-2H3

93-51-6 Well-known Company Product Price

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  • (Code)Product description
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  • Alfa Aesar

  • (A13603)  2-Methoxy-4-methylphenol, 98+%   

  • 93-51-6

  • 10g

  • 223.0CNY

  • Detail
  • Alfa Aesar

  • (A13603)  2-Methoxy-4-methylphenol, 98+%   

  • 93-51-6

  • 50g

  • 631.0CNY

  • Detail
  • Alfa Aesar

  • (A13603)  2-Methoxy-4-methylphenol, 98+%   

  • 93-51-6

  • 250g

  • 2925.0CNY

  • Detail

93-51-6SDS

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 2-Methoxy-4-methylphenol

1.2 Other means of identification

Product number -
Other names Homoguaiacol

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:93-51-6 SDS

93-51-6Synthetic route

vanillin
121-33-5

vanillin

2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

Conditions
ConditionsYield
With formic acid; palladium and silver nanoparticles over graphitic carbon nitride surface In water at 20℃; for 4h; Catalytic behavior; Reagent/catalyst; Temperature; Sealed tube; Irradiation;100%
With hydrogen; acetic acid; palladium on activated charcoal at 55℃; for 24h;99%
With hydrogen In water at 150℃; under 3750.38 Torr; for 5h; Reagent/catalyst; Temperature; Pressure; Time; Solvent; Autoclave;99.8%
vanillin
121-33-5

vanillin

A

2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

B

4-hydroxymethyl-2-methoxyphenol
498-00-0

4-hydroxymethyl-2-methoxyphenol

Conditions
ConditionsYield
With hydrogen In water at 70℃; Catalytic behavior;A 99.9%
B n/a
With hydrogen In water at 20 - 100℃; under 3750.38 Torr; for 1h; Kinetics; Reagent/catalyst; Temperature; Pressure; Autoclave;A 90.9%
B 9.1%
With 2 wt% Pd/C; hydrogen In water at 20 - 100℃; under 3750.38 Torr; for 1h; Kinetics; Reagent/catalyst; Autoclave;A 21.8%
B 78.3%
2-bromo-p-cresol
6627-55-0

2-bromo-p-cresol

sodium methylate
124-41-4

sodium methylate

2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

Conditions
ConditionsYield
With Methyl formate; copper(l) chloride In methanol at 110℃; for 2h; Autoclave;98%
In methanol at 200℃; under 120012 Torr; for 0.0333333h; Temperature; Pressure; Time; Autoclave;13.38 g
4-hydroxymethyl-2-methoxyphenol
498-00-0

4-hydroxymethyl-2-methoxyphenol

2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

Conditions
ConditionsYield
Stage #1: 4-hydroxymethyl-2-methoxyphenol With ammonium formate In ethanol; water at 22℃; for 0.166667h;
Stage #2: With formic acid In ethanol; water at 22℃; for 1h; Catalytic behavior; Reagent/catalyst; Temperature; Solvent; chemoselective reaction;
95%
With lithium aluminium tetrahydride In tetrahydrofuran; chlorobenzene for 3h; Heating;87%
With triethylsilane; palladium dichloride In ethanol at 20℃; for 0.166667h; Inert atmosphere;96 %Chromat.
1-(allyloxy)-2-methoxy-4-methylbenzene
201359-55-9

1-(allyloxy)-2-methoxy-4-methylbenzene

2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

Conditions
ConditionsYield
Stage #1: 1-(allyloxy)-2-methoxy-4-methylbenzene With tert.-butyl lithium In diethyl ether; pentane at -78℃; for 2h; Inert atmosphere;
Stage #2: With methanol In diethyl ether; pentane at -78℃; Inert atmosphere;
88%
4-hydroxy-3-methoxyphenylacetonitrile
4468-59-1

4-hydroxy-3-methoxyphenylacetonitrile

2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

Conditions
ConditionsYield
Stage #1: 4-hydroxy-3-methoxyphenylacetonitrile With 15-crown-5; sodium In tetrahydrofuran; hexane at 0℃; for 0.333333h; Birch Reduction; Inert atmosphere;
Stage #2: With water In tetrahydrofuran; hexane at 0℃; for 1h; Birch Reduction; Inert atmosphere;
Stage #3: With hydrogenchloride In water pH=1; chemoselective reaction;
84%
Stage #1: 4-hydroxy-3-methoxyphenylacetonitrile With 15-crown-5; sodium In tetrahydrofuran; hexane at 0℃; for 0.333333h; Inert atmosphere;
Stage #2: With water In tetrahydrofuran; hexane at 0℃; for 1h;
74%
1-methoxy-3-methyl-benzene
100-84-5

1-methoxy-3-methyl-benzene

A

2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

B

1-hydroxy-4-methoxy-2-methylbenzene
5307-05-1

1-hydroxy-4-methoxy-2-methylbenzene

C

2-methyl-6-methoxyphenol
2896-67-5

2-methyl-6-methoxyphenol

Conditions
ConditionsYield
With wild type cytochrome P450 CYP102A1 variants RLYF/A330P; oxygen; NADPH Reagent/catalyst; Enzymatic reaction;A 11%
B 80%
C 7%
C28H44O4P2

C28H44O4P2

2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

Conditions
ConditionsYield
With chlorobis(ethylene)rhodium(I) dimer; hydrogen In 1,4-dioxane at 150℃; under 7757.43 Torr; Pressure; Reagent/catalyst;79%
Propionic acid 2-methoxy-4-methyl-phenyl ester
108439-89-0

Propionic acid 2-methoxy-4-methyl-phenyl ester

A

2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

B

hydroxy-5 methoxy-4 methyl-2 propiophenone
91970-98-8

hydroxy-5 methoxy-4 methyl-2 propiophenone

C

propionyloxy-5 methoxy-4 methyl-2 propiophenone
108439-90-3

propionyloxy-5 methoxy-4 methyl-2 propiophenone

Conditions
ConditionsYield
With aluminium trichloride In dichloromethane at 20℃; for 8h;A 32%
B 59%
C 4%
With aluminium trichloride In dichloromethane at 0℃; for 8h;A 32%
B 49%
C 20%
2-(2-methoxy-4-methylphenoxy)acetic acid
6270-23-1

2-(2-methoxy-4-methylphenoxy)acetic acid

2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

Conditions
ConditionsYield
Stage #1: 2-(2-methoxy-4-methylphenoxy)acetic acid With diphenyl-phosphinic acid; triethylamine In N,N-dimethyl-formamide; toluene for 3h; Curtius-rearrangement; Heating;
Stage #2: With water In N,N-dimethyl-formamide; toluene Heating; Further stages.;
59%
vanillin
121-33-5

vanillin

A

p-cresol
106-44-5

p-cresol

B

2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

Conditions
ConditionsYield
With hydrogen In water at 100℃; under 15001.5 Torr; for 3h; Autoclave;A 6.9%
B 53.7%
With isopropyl alcohol at 140℃; for 15h; Reagent/catalyst; Autoclave;
2,4'-dimethoxy-4-methyldiphenyl ether
23990-91-2

2,4'-dimethoxy-4-methyldiphenyl ether

sodium methylate
124-41-4

sodium methylate

A

2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

B

1,1,4,4-tetramethoxycyclohexa-2,5-diene
15791-03-4

1,1,4,4-tetramethoxycyclohexa-2,5-diene

Conditions
ConditionsYield
In methanol anodic oxidation; Pt foil anode and catode;A n/a
B 53%
4-hydroxymethyl-2-methoxyphenol
498-00-0

4-hydroxymethyl-2-methoxyphenol

A

2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

B

4,4’-dihydroxy-3,3’-dimethoxybibenzyl
18256-53-6

4,4’-dihydroxy-3,3’-dimethoxybibenzyl

Conditions
ConditionsYield
With triphenylphosphine In 1,4-dioxane at 200℃; for 16h; Autoclave; Inert atmosphere;A 33%
B 53%
vanillin
121-33-5

vanillin

A

p-cresol
106-44-5

p-cresol

B

2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

C

4-hydroxymethyl-2-methoxyphenol
498-00-0

4-hydroxymethyl-2-methoxyphenol

Conditions
ConditionsYield
With hydrogen In water at 100℃; under 15001.5 Torr; for 3h; Autoclave;A 6.9%
B 52.3%
C 6.63%
With hydrogen In water at 100℃; under 15001.5 Torr; for 3h; Autoclave;A 6.9%
B 52.9%
C 6.9%
With hydrogen In water at 100℃; under 15001.5 Torr; for 3h; Autoclave;A 5.3%
B 49.9%
C 11.8%
1,2-dimethoxy-4-methylbenzene
494-99-5

1,2-dimethoxy-4-methylbenzene

A

5-methyl-2-methoxyphenol
1195-09-1

5-methyl-2-methoxyphenol

B

2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

C

4-methyl-1,2-dihydroxybenzene
452-86-8

4-methyl-1,2-dihydroxybenzene

Conditions
ConditionsYield
With orcinol; Acetobacterium dehalogenans veratrol-O-demethylase; Desulfitobacterium hafniense methyltransferase dhaf4611 In aq. buffer at 25℃; for 24h; pH=6.5; Inert atmosphere; Enzymatic reaction; regioselective reaction;A 35%
B 52%
C 13%
3,3'-dimethoxy-5,5'-dimethyl-[1,1'-biphenyl]-2,2'-diol
13990-86-8

3,3'-dimethoxy-5,5'-dimethyl-[1,1'-biphenyl]-2,2'-diol

2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

Conditions
ConditionsYield
Stage #1: 3,3'-dimethoxy-5,5'-dimethyl-[1,1'-biphenyl]-2,2'-diol With Chlorodiisopropylphosphane; sodium hydride In 1,4-dioxane at 20℃;
Stage #2: With chlorobis(ethylene)rhodium(I) dimer; hydrogen In 1,4-dioxane at 150℃; under 2585.81 Torr;
50%
Multi-step reaction with 2 steps
1: triethylamine
2: hydrogen; chlorobis(ethylene)rhodium(I) dimer / 1,4-dioxane / 150 °C / 7757.43 Torr
View Scheme
2-methoxy-p-tolyl acetate
879-67-4

2-methoxy-p-tolyl acetate

A

2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

B

hydroxy-5 methoxy-4 methyl-2 acetophenone
6948-37-4

hydroxy-5 methoxy-4 methyl-2 acetophenone

C

acetoxy-5 methoxy-4 methyl-2 acetophenone
35684-86-7

acetoxy-5 methoxy-4 methyl-2 acetophenone

Conditions
ConditionsYield
With aluminium trichloride In dichloromethane at 0℃; for 8h;A 32%
B 45%
C 15%
2-methoxy-4-methylphenoxybenzene
128837-56-9

2-methoxy-4-methylphenoxybenzene

A

2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

B

cyclohexane
110-82-7

cyclohexane

C

methyl cyclohexane
82166-21-0

methyl cyclohexane

Conditions
ConditionsYield
With hydrogen In decalin at 200℃; under 75007.5 Torr; for 3h;A 45%
B n/a
C n/a
allyl 2-bromo-6-methoxy-4-methylphenyl ether

allyl 2-bromo-6-methoxy-4-methylphenyl ether

A

2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

B

C11H14O2

C11H14O2

Conditions
ConditionsYield
Stage #1: allyl 2-bromo-6-methoxy-4-methylphenyl ether With tert.-butyl lithium In diethyl ether; pentane at -78℃; Inert atmosphere;
Stage #2: With N,N,N,N,-tetramethylethylenediamine In diethyl ether; pentane at -78 - 0℃; Inert atmosphere;
Stage #3: With water Inert atmosphere;
A 35%
B 42%
3,3'-dimethoxy-5,5'-dimethyl-[1,1'-biphenyl]-2,2'-diol
13990-86-8

3,3'-dimethoxy-5,5'-dimethyl-[1,1'-biphenyl]-2,2'-diol

A

2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

B

5,5'-Dimethyl-1,1'-biphenyl-2,2',3,3'-tetrol
3598-32-1

5,5'-Dimethyl-1,1'-biphenyl-2,2',3,3'-tetrol

C

2-methoxy-phenol
90-05-1

2-methoxy-phenol

D

3'-methoxy-5,5'-dimethyl-biphenyl-2,3,2'-triol

3'-methoxy-5,5'-dimethyl-biphenyl-2,3,2'-triol

Conditions
ConditionsYield
With sulfuric acid; water at 224.84℃; under 21752.2 Torr; for 1.5h; Inert atmosphere; Autoclave;A 7%
B 9%
C 12%
D 42%
vanillin
121-33-5

vanillin

A

2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

B

5-[(4-hydroxy-3-methoxyphenyl)methyl]-2-methoxy-4-methylphenol
38768-71-7

5-[(4-hydroxy-3-methoxyphenyl)methyl]-2-methoxy-4-methylphenol

Conditions
ConditionsYield
With triethylsilane; zinc(II) iodide In 1,2-dichloro-ethane at 20℃; for 7h;A 28%
B 34%
3-methoxy-4-(phenylmethoxy)benzaldehyde
2426-87-1

3-methoxy-4-(phenylmethoxy)benzaldehyde

2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

Conditions
ConditionsYield
With Pd-BaSO4; ethyl acetate Hydrogenation;
2-bromo-p-cresol
6627-55-0

2-bromo-p-cresol

2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

Conditions
ConditionsYield
With potassium hydroxide at 150 - 155℃; under 11032.6 Torr;
5-bromo-2-methoxy-4-methylphenol
83387-13-7

5-bromo-2-methoxy-4-methylphenol

2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

pinoresinol
7452-03-1

pinoresinol

A

2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

B

2-methoxy-4-propenylphenol
97-54-1

2-methoxy-4-propenylphenol

C

2-methoxy-phenol
90-05-1

2-methoxy-phenol

Conditions
ConditionsYield
Bei der trockenen Destillation;
vanillin
121-33-5

vanillin

A

2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

B

6,3'-dimethoxy-4-methyl-3,4'-methanediyl-di-phenol

6,3'-dimethoxy-4-methyl-3,4'-methanediyl-di-phenol

Conditions
ConditionsYield
With palladium on activated charcoal; acetic acid Hydrogenation;
dimethyl sulfate
77-78-1

dimethyl sulfate

4-methyl-1,2-dihydroxybenzene
452-86-8

4-methyl-1,2-dihydroxybenzene

2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

Conditions
ConditionsYield
With alkali at 50 - 60℃;
sodium methyl sulfate
512-42-5

sodium methyl sulfate

4-methyl-1,2-dihydroxybenzene
452-86-8

4-methyl-1,2-dihydroxybenzene

A

2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

B

1,2-dimethoxy-4-methylbenzene
494-99-5

1,2-dimethoxy-4-methylbenzene

Conditions
ConditionsYield
With potassium hydroxide
methanol
67-56-1

methanol

2-Diazo-4-methylphenol
87842-95-3

2-Diazo-4-methylphenol

2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

Conditions
ConditionsYield
With sulfuric acid at 0℃; for 24h; Mechanism; Irradiation;7.9 % Chromat.
3-methoxy-4-nitrotoluene
38512-82-2

3-methoxy-4-nitrotoluene

A

2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

B

2-nitro-5-methylphenol
700-38-9

2-nitro-5-methylphenol

Conditions
ConditionsYield
With sodium hydroxide; tert-butyl alcohol In water Quantum yield; Irradiation;
2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

allyl bromide
106-95-6

allyl bromide

1-(allyloxy)-2-methoxy-4-methylbenzene
201359-55-9

1-(allyloxy)-2-methoxy-4-methylbenzene

Conditions
ConditionsYield
With potassium carbonate In acetone for 12h; Heating;100%
With potassium carbonate; sodium iodide In acetone for 15h; Reflux; Inert atmosphere;96%
With potassium carbonate In acetone for 6h; Heating;95%
formaldehyd
50-00-0

formaldehyd

2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

dimethyl amine
124-40-3

dimethyl amine

6<(dimethylamino)methyl>-2-methoxy-4-methylphenol
123752-64-7

6<(dimethylamino)methyl>-2-methoxy-4-methylphenol

Conditions
ConditionsYield
In water for 1.5h;100%
2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

C14H13IN3Pol

C14H13IN3Pol

C22H22N3O2Pol

C22H22N3O2Pol

Conditions
ConditionsYield
With pyridine; copper(I) bromide dimethylsulfide complex; sodium carbonate In acetonitrile at 75℃; for 48h; Inert atmosphere; solid phase reaction;100%
2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

C8H7(2)H3O2
7329-56-8

C8H7(2)H3O2

Conditions
ConditionsYield
With perchloric acid; d(4)-methanol at 75℃; for 96h; Inert atmosphere;100%
With sulfuryl dichloride; water-d2 at 100℃; for 30h; Microwave irradiation; Sealed tube;100 %Chromat.
2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

4-methyl-1,2-dihydroxybenzene
452-86-8

4-methyl-1,2-dihydroxybenzene

Conditions
ConditionsYield
With hydrogenchloride In water at 250℃; under 37503.8 Torr; for 3h; Autoclave; Inert atmosphere; Green chemistry;99%
With aluminium(III) iodide; tetra-(n-butyl)ammonium iodide In cyclohexane for 0.7h; Heating;98%
With aluminium(III) iodide In dimethyl sulfoxide; acetonitrile at 80℃; for 18h;96%
2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

acetic anhydride
108-24-7

acetic anhydride

2-methoxy-p-tolyl acetate
879-67-4

2-methoxy-p-tolyl acetate

Conditions
ConditionsYield
With zirconium(IV) chloride at 20℃; for 0.25h;99%
With sulfuric acid
With sulfuric acid at 100℃;
2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

3-methylphenylsulfonyl chloride
1899-93-0

3-methylphenylsulfonyl chloride

2-Methoxy-4-methylphenyl 3-methylbenzenesulfonate

2-Methoxy-4-methylphenyl 3-methylbenzenesulfonate

Conditions
ConditionsYield
With triethylamine In hexane; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran99%
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

2-methoxy-4-methylphenyl trifluoromethanesulfonate
138642-33-8

2-methoxy-4-methylphenyl trifluoromethanesulfonate

Conditions
ConditionsYield
With triethylamine In dichloromethane at -78 - 20℃; for 14h; Inert atmosphere;99%
Stage #1: 2-Methoxy-4-methylphenol With pyridine In dichloromethane at 0℃; for 0.0833333h; Inert atmosphere; Schlenk technique;
Stage #2: trifluoromethylsulfonic anhydride In dichloromethane at 0 - 20℃; for 18h; Inert atmosphere; Schlenk technique;
78%
2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

4-fluorobenzonitrile
1194-02-1

4-fluorobenzonitrile

4-(2-methoxy-4-methylphenoxy)benzonitrile
897036-73-6

4-(2-methoxy-4-methylphenoxy)benzonitrile

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl acetamide at 100℃; for 30h;99%
2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

2-fluorobenzonitrile
394-47-8

2-fluorobenzonitrile

2-(2-methoxy-4-methyl-phenoxy)-benzonitrile
928302-73-2

2-(2-methoxy-4-methyl-phenoxy)-benzonitrile

Conditions
ConditionsYield
With caesium carbonate In dimethyl amine at 100℃; for 30h;99%
titanium(IV) isopropylate
546-68-9

titanium(IV) isopropylate

2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

[(2-methoxy-4-methylphenoxy)2Ti(isopropoxy)2]
1394844-98-4

[(2-methoxy-4-methylphenoxy)2Ti(isopropoxy)2]

Conditions
ConditionsYield
In cyclohexane at 20℃; Inert atmosphere; Schlenk technique;99%
2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

carbon dioxide
124-38-9

carbon dioxide

2-hydroxy-3-methoxy-5-methylbenzoic acid
4386-42-9

2-hydroxy-3-methoxy-5-methylbenzoic acid

Conditions
ConditionsYield
Stage #1: 2-Methoxy-4-methylphenol; carbon dioxide With potassium carbonate at 200℃; under 41372.9 Torr; for 4.5h; Kolbe-Schmitt reaction; Autoclave;
Stage #2: With hydrogenchloride In water at 20℃; pH=1;
98%
With potassium carbonate at 200℃; under 41371.8 Torr; for 4h; Carboxylation; Kolbe-Schmitt carboxylation;
methanol
67-56-1

methanol

4-penten-3-one
1629-58-9

4-penten-3-one

2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

(1SR,4SR,7SR)-3,3-dimethoxy-5-methyl-7-propionylbicyclo[2.2.2]oct-5-en-2-one

(1SR,4SR,7SR)-3,3-dimethoxy-5-methyl-7-propionylbicyclo[2.2.2]oct-5-en-2-one

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene at 20℃; for 1h;98%
2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

trimethylsilylazide
4648-54-8

trimethylsilylazide

(4-methyl-2-methoxyphenoxy)trimethylsilane
132114-79-5

(4-methyl-2-methoxyphenoxy)trimethylsilane

Conditions
ConditionsYield
tetrabutylammomium bromide at 30℃; for 4h;98%
2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

Isopropyl isocyanate
1795-48-8

Isopropyl isocyanate

C12H17NO3
956219-14-0

C12H17NO3

Conditions
ConditionsYield
With dmap In tetrahydrofuran Heating;98%
2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

benzyl bromide
100-39-0

benzyl bromide

1-(benzyloxy)-2-methoxy-4-methylbenzene
78136-55-7

1-(benzyloxy)-2-methoxy-4-methylbenzene

Conditions
ConditionsYield
With potassium carbonate In acetonitrile for 18h; Reflux;98%
With potassium carbonate In acetonitrile for 18h; Reflux;98%
With potassium carbonate In acetone at 50℃; for 12h; Inert atmosphere;96%
Stage #1: 2-Methoxy-4-methylphenol With sodium hydride In DMF (N,N-dimethyl-formamide) at 0℃; for 0.5h;
Stage #2: benzyl bromide With tetrabutylammomium bromide In DMF (N,N-dimethyl-formamide) at 0 - 20℃;
1-bromo-4-butene
5162-44-7

1-bromo-4-butene

2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

1-(but-3-enyloxy)-2-methoxy-4-methylbenzene
1140923-64-3

1-(but-3-enyloxy)-2-methoxy-4-methylbenzene

Conditions
ConditionsYield
With potassium carbonate In acetonitrile for 12h; Reflux;98%
2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

2-N,N-Dimethylaminonaphthalene
2436-85-3

2-N,N-Dimethylaminonaphthalene

2-(2-(dimethylamino)naphthalen-1-yl)-6-methoxy-4-methylphenol

2-(2-(dimethylamino)naphthalen-1-yl)-6-methoxy-4-methylphenol

Conditions
ConditionsYield
With iron(III) chloride; di-tert-butyl peroxide; trifluoroacetic acid at 20℃; for 24h; chemoselective reaction;98%
With 1,1,1,3',3',3'-hexafluoro-propanol; periodic acid In nitromethane; N,N-dimethyl-formamide at 20℃; for 0.5h;34%
formaldehyd
50-00-0

formaldehyd

2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

2,2'-dihydroxy-3,3'-dimethoxy-5,5'-dimethyl-diphenylmethane
1620-70-8

2,2'-dihydroxy-3,3'-dimethoxy-5,5'-dimethyl-diphenylmethane

Conditions
ConditionsYield
With sodium hydroxide for 2.5h; Dimerization;97%
With zinc(II) acetate dihydrate for 16h; Inert atmosphere; Reflux; regioselective reaction;41%
With zinc(II) acetate dihydrate for 16h; Reflux; Inert atmosphere;41%
With zinc diacetate
2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

3,3'-dimethoxy-5,5'-dimethylbiphenyl-2,2'-diol

3,3'-dimethoxy-5,5'-dimethylbiphenyl-2,2'-diol

Conditions
ConditionsYield
With copper diacetate; ethylene glycol at 75℃; for 12h; Green chemistry;97%
2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

N-[(trifluoromethyl)sulfanyl]aniline
1045821-71-3

N-[(trifluoromethyl)sulfanyl]aniline

2-methoxy-4-methyl-5-(trifluoromethylthio)phenol

2-methoxy-4-methyl-5-(trifluoromethylthio)phenol

Conditions
ConditionsYield
With trifluorormethanesulfonic acid In dichloromethane at 20℃; regioselective reaction;97%
2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

methyl iodide
74-88-4

methyl iodide

1,2-dimethoxy-4-methylbenzene
494-99-5

1,2-dimethoxy-4-methylbenzene

Conditions
ConditionsYield
Stage #1: 2-Methoxy-4-methylphenol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Sealed tube;
Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 60℃; Sealed tube;
96%
With sodium hydroxide In N,N-dimethyl acetamide at 25℃; Rate constant;
methanol
67-56-1

methanol

4-penten-3-one
1629-58-9

4-penten-3-one

2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

(1R,4R)-3,3-Dimethoxy-5-methyl-7-propionyl-bicyclo[2.2.2]oct-5-en-2-one

(1R,4R)-3,3-Dimethoxy-5-methyl-7-propionyl-bicyclo[2.2.2]oct-5-en-2-one

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene at 20℃; Diels-Alder reaction;96%
With isosorbide dinitrate88%
2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

p-Chlorothiophenol
106-54-7

p-Chlorothiophenol

2-methoxy-4-methyl-6-((4-nitrophenyl)thio)phenol

2-methoxy-4-methyl-6-((4-nitrophenyl)thio)phenol

Conditions
ConditionsYield
With nitronium tetrafluoborate; oxygen In sulfolane at 20℃; for 24h; Sealed tube;96%
2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

propionyl chloride
79-03-8

propionyl chloride

hydroxy-5 methoxy-4 methyl-2 propiophenone
91970-98-8

hydroxy-5 methoxy-4 methyl-2 propiophenone

Conditions
ConditionsYield
With aluminium trichloride In dichloromethane at 20℃; for 2h;95%
2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

N,N-diethylcarbamyl chloride
88-10-8

N,N-diethylcarbamyl chloride

N,N-diethyl-1-carbamyloxy-2-methoxy-4-methylbenzene
628339-15-1

N,N-diethyl-1-carbamyloxy-2-methoxy-4-methylbenzene

Conditions
ConditionsYield
Stage #1: 2-Methoxy-4-methylphenol With sodium hydride In tetrahydrofuran at 20℃; for 2h;
Stage #2: N,N-diethylcarbamyl chloride In tetrahydrofuran at 20℃; for 8h;
95%
With sodium hydride In tetrahydrofuran at 20℃;95%

93-51-6Relevant articles and documents

Mild-temperature hydrodeoxygenation of vanillin over porous nitrogen-doped carbon black supported nickel nanoparticles

Nie, Renfeng,Yang, Huanhuan,Zhang, Haifu,Yu, Xiaolong,Lu, Xinhuan,Zhou, Dan,Xia, Qinghua

, p. 3126 - 3134 (2017)

Porous nitrogen-doped carbon black (NCB) was synthesized by facile carbonization of carbon black (CB) coated with polypyrrole (CB@polypyrrole) and used as a support for Ni nanoparticles (NPs). The microstructure, reducibility and crystallinity of the as-synthesized materials were investigated by transmission electron microscopy (TEM), H2-TPR/TPD, X-ray photoelectron spectroscopy (XPS) and X-ray diffraction (XRD). It was found that surface nitrogen species on NCB significantly promote the decomposition of the nickel precursor and the reduction of nickel oxide, and improve the stability of metallic Ni in ambient atmosphere. In the selective hydrodeoxygenation (HDO) of vanillin in the aqueous phase at low hydrogen pressure (0.5 MPa) and mild temperature (150 °C), Ni/NCB shows much higher activity than N-free catalysts. This is ascribed to the higher reducibility, the lower oxidation state of Ni NPs and the enhanced hydrogen spillover of Ni to the support. Moreover, the Ni/NCB catalyst is relatively cheap and easy to scale-up the production of, thus achieving a low-cost transformation of biomass to bio-oils.

Silica/titania composite-supported NiCo catalysts with combined catalytic effects for phenol hydrogenation under fast and mild conditions

Li, Yucheng,Liu, Jing,He, Jing,Wang, Luying,Lei, Jiandu

, (2020)

The effect of titanium as a promoter for the nickel-cobalt/silica-titania (NiCo/Si-Ti) catalyst in the hydrogenation of phenol was comparatively studied. In the phenol hydrogenation under mild reaction conditions (1 MPa H2 pressure and 100 °C), the Ti-promoter induces the formation of the Coδ??OV?Ti3+ active sites and enhances the hydrogenation activity of the NiCo/Si catalyst to convert phenol to cyclohexanol. The catalytic hydrogenation with the optimal composition of the NiCo/Si-1.0Ti (Si:Ti ratio of 8.5:1) catalyst was completed within 1 h (conversion 98.2 % and selectivity >99 %), which was more efficiently than that with other Ti-doped catalysts and NiCo/Si as baseline, indicating a strong positive synergistic effect between the metal (Ni-Co) and support (Ti-Si) components of the catalyst in this reaction. Additionally, the kinetics, pathway and catalytic mechanism of the hydrogenation of phenol are also examined. Furthermore, the NiCo/Si-1.0Ti catalysts also showed a good performance at reducing the unstable oxygenated compounds in the bio-oil.

Method for catalyzing hydrodeoxygenation of vanillin by using MOF-based nano composite material

-

Paragraph 0024; 0031-0033; 0040-0042; 0049-0050, (2021/07/31)

The invention discloses a method for catalyzing hydrodeoxygenation of vanillin by using an MOF-based nano composite material, which is characterized in that a UiO-series MOFs material with relatively good hydrothermal stability is used as a carrier and is combined with metal nanoparticles to catalyze hydrodeoxygenation of vanillin. The method solves some problems of a traditional catalyst carrier in the hydrodeoxygenation reaction of vanillin, such as self-sintering, carbon deposition, leaching of active components, and great influence on activity in the reaction process. According to the invention, the active component can be well anchored, the performance of the active component can be promoted, the high yield of the target deoxidation product can be achieved, and the excellent catalysis effect can be achieved.

In situhydrodeoxygenation of vanillin over Ni-Co-P/HAP with formic acid as a hydrogen source

Duan, Mingxing,Cheng, Qingyan,Wang, Mingming,Wang, Yanji

, p. 10996 - 11003 (2021/03/23)

A new noble metal-free Ni-Co-P/HAP (hydroxyapatite) amorphous alloy catalyst was synthesized by an impregnation-chemical reduction method; the structure and properties of the catalysts were characterized by XRD, SEM, BET, XPS and DSC. Based on the model of the hydrodeoxygenation (HDO) of vanillin to 2-methoxy-4-methylphenol (MMP) with formic acid as a hydrogen source, the catalytic performance of the catalyst was studied. The results found that the Ni-Co-P/HAP catalyst exhibited excellent catalytic activity for thein situHDO reaction of vanillin compared with Ni-P and Ni-Co-P. The conversion of vanillin could be high to 97.86% with MMP selectivity of 93.97% under optimized reaction conditions. In addition, mechanism studies have shown that the side reaction of carbocation and vanillyl alcohol (HMP) condensation can be effectively reduced with increasing the hydrogenation rate, thereby the selectivity of MMP was effectively increased.

Encapsulated Ni-Co alloy nanoparticles as efficient catalyst for hydrodeoxygenation of biomass derivatives in water

Chen, Chun,Gong, Wanbing,Han, Miaomiao,Wang, Dongdong,Wang, Guozhong,Zhang, Haimin,Zhang, Jifang,Zhang, Yunxia,Zhao, Huijun

, p. 2027 - 2037 (2021/09/02)

Catalytic hydrodeoxygenation (HDO) is one of the most promising strategies to transform oxygen-rich biomass derivatives into high value-added chemicals and fuels, but highly challenging due to the lack of highly efficient nonprecious metal catalysts. Herein, we report for the first time of a facile synthetic approach to controllably fabricate well-defined Ni-Co alloy NPs confined on the tip of N-CNTs as HDO catalyst. The resultant Ni-Co alloy catalyst possesses outstanding HDO performance towards biomass-derived vanillin into 2-methoxy-4-methylphenol in water with 100% conversion efficiency and selectivity under mild reaction conditions, surpassing the reported high performance nonprecious HDO catalysts. Impressively, our experimental results also unveil that the Ni-Co alloy catalyst can be generically applied to catalyze HDO of vanillin derivatives and other aromatic aldehydes in water with 100% conversion efficiency and over 90% selectivity. Importantly, our DFT calculations and experimental results confirm that the achieved outstanding HDO catalytic performance is due to the greatly promoted selective adsorption and activation of C=O, and desorption of the activated hydrogen species by the synergism of the alloyed Ni-Co NPs. The findings of this work affords a new strategy to design and develop efficient transition metal-based catalysts for HDO reactions in water.

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