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90-05-1

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90-05-1 Usage

Chemical Description

Guaiacol is a naturally occurring organic compound that is commonly found in wood smoke and used as a flavoring agent.

Chemical Properties

Guaiacol appears as white or slightly yellow crystals or colorless to light yellow transparent oily liquid. It has a distinctive scent. It is slightly soluble in water and benzene, also easily soluble in glycerol. And it is miscible with ethanol, ether, chloroform, oil and glacier acetic acid. Guaiacol is a phenolic natural product first isolated from Guaiac resin and the oxidation of lignin. It is also present in wood smoke, as a product of pyrolysis of lignin.

Occurrence

Detected in the distillation product from guaiac resin; guaiacol is found in castoreum oil, in the essential oil from fowers of Pandanus odoratissimus L , in the distillation waters of orange leaves, in the essential oil of Ruta Montana L and in the essential oil of tobacco leaves Also reported found in lemon peel oil, bog blueberry, asparagus, cabbage, celery, onion, chive, tomato, peppermint oil, rye bread, Parmesan cheese, butter, smoked fsh, meats, barley, dried bonito, malt, hardwood smoke, cognac, beer, brandy, rum, whiskies, sherry, grape wines, cocoa, coffee, tea, peanuts, popcorn, soybeans, avocado, beans, mushroom, sesame seed, mango, tamarind, rice dill, licorice, corn oil, cuttlefsh and other sources

Uses

Different sources of media describe the Uses of 90-05-1 differently. You can refer to the following data:
1. Guaiacol is a precursor of vanillin and santalidol (a synthetic sandal- wood fragrance). it is obtained from wood tar by the destructive distillation of hardwood, by the distillation of the phenol fraction of coal tar, or through the use of o-dichlorobenzene. it is processed to yield vanillin.
2. Synthetic flavors, medicine (expectorant).
3. A phenolic natural product and reducing co-substrate for COX reactions.

Definition

ChEBI: Guaiacol is a monomethoxybenzene that consists of phenol with a methoxy substituent at the ortho position. It has a role as an expectorant, a disinfectant, a plant metabolite and an EC 1.1.1.25 (shikimate dehydrogenase) inhibitor. It is functionally related to a catechol.

Preparation

Guaiacol can be obtained by diazotization and hydrolysis of anthranium anisole or obtained from fractionated of wood oil.In the nature of guaiacol is presented in the guaiacum or pine oil. In the creosote oil obtained from wood dry distillation, guaiacol is the major ingredient. This product could be obtained through fractional distillation of creosote oil. Japan Osaka Refining Company takes o-nitrochlorobenzene as raw material, first synthesizes o-nitroanisole, and then reduces it to o-anisidine, and finally obtains the goods. China's production method is roughly the same. Ingredient consumption quota: 1250 kg / t of amino-containing anisole, 1500 kg / t of sulfuric acid (93%), 700 kg / t of sodium nitrite and 400 kg / t of copper sulfate.

Aroma threshold values

Detection: 3 to 31 ppb; aroma characteristics at 1.0%: phenolic, smoky, spicy, medicinal, vanilla, savory meaty, woody with a bourbon whiskey casky nuance.

Taste threshold values

Taste characteristics at 2.0 ppm: woody, phenolic, bacon, savory, smoky and medicinal.

General Description

Guaiacol is a colorless to amber crystals or liquid. Density (of solid) 1.129 g / cm3. Solidifies at 28°C (82.4°F), but may remain liquid for a long time even at a much lower temperature. Slightly water soluble . Soluble in aqueous sodium hydroxide. It is an agent thought to have disinfectant properties and used as an expectorant.

Air & Water Reactions

Sensitive to air and light (darkens). Slightly water soluble.

Reactivity Profile

Guaiacol may react with oxidizing materials. Guaiacol forms salts readily with bases.

Fire Hazard

Guaiacol is combustible.

Biochem/physiol Actions

Guaiacol, along with 2,4,6-trichloroanisole, is responsible for cork taint in wine. A method has been developed for extraction and quantitation of the two compounds.

Synthesis

Obtained from hardwood tar or synthetically from o-nitrophenol via o-anisidine.

Purification Methods

Crystallise guaiacol from *benzene/pet ether or distil it in a vacuum. [Beilstein 6 H 768, 6 IV 5563.]

Toxicity evaluation

LD50:900 mg / kg (rat, subcutaneous).LD50: 3.7 mg / kg (rabbit, intravenously).Oral administration of large amount can stimulate the esophagus and stomach, resulting in heart failure, collapse and death.

Check Digit Verification of cas no

The CAS Registry Mumber 90-05-1 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 0 respectively; the second part has 2 digits, 0 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 90-05:
(4*9)+(3*0)+(2*0)+(1*5)=41
41 % 10 = 1
So 90-05-1 is a valid CAS Registry Number.
InChI:InChI=1/C7H8O2/c1-9-7-5-3-2-4-6(7)8/h2-5,8H,1H3

90-05-1 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (M0121)  Guaiacol  >98.0%(GC)

  • 90-05-1

  • 25g

  • 124.00CNY

  • Detail
  • TCI America

  • (M0121)  Guaiacol  >98.0%(GC)

  • 90-05-1

  • 500g

  • 442.00CNY

  • Detail
  • Alfa Aesar

  • (A16319)  2-Methoxyphenol, 98+%   

  • 90-05-1

  • 250g

  • 317.0CNY

  • Detail
  • Alfa Aesar

  • (A16319)  2-Methoxyphenol, 98+%   

  • 90-05-1

  • 1000g

  • 801.0CNY

  • Detail
  • Alfa Aesar

  • (A16319)  2-Methoxyphenol, 98+%   

  • 90-05-1

  • 5000g

  • 3165.0CNY

  • Detail
  • Sigma-Aldrich

  • (PHR1136)  Guaiacol  pharmaceutical secondary standard; traceable to USP and PhEur

  • 90-05-1

  • PHR1136-1.5G

  • 732.19CNY

  • Detail
  • Sigma-Aldrich

  • (Y0000619)  Guaiacol  European Pharmacopoeia (EP) Reference Standard

  • 90-05-1

  • Y0000619

  • 1,880.19CNY

  • Detail
  • USP

  • (1300004)  Guaiacol  United States Pharmacopeia (USP) Reference Standard

  • 90-05-1

  • 1300004-1G

  • 4,326.66CNY

  • Detail

90-05-1SDS

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 guaiacol

1.2 Other means of identification

Product number -
Other names Guaiacol

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:90-05-1 SDS

90-05-1Synthetic route

2-(2-methoxyphenoxy)-1-(4-methoxyphenyl)ethan-1-one
19513-80-5

2-(2-methoxyphenoxy)-1-(4-methoxyphenyl)ethan-1-one

A

2-methoxy-phenol
90-05-1

2-methoxy-phenol

B

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With formic acid; N-ethyl-N,N-diisopropylamine; Lumogen F Orange 240 In acetonitrile at 25℃; for 8h; Reagent/catalyst; UV-irradiation; Inert atmosphere;A 99%
B 99%
With formic acid; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; N-ethyl-N,N-diisopropylamine In ethanol at 20℃; Irradiation; chemoselective reaction;A 95%
B 72%
With formic acid; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 12h; Reagent/catalyst; Irradiation; chemoselective reaction;A 89%
B 88%
4-iodoanisol
529-28-2

4-iodoanisol

2-methoxy-phenol
90-05-1

2-methoxy-phenol

Conditions
ConditionsYield
With glycolic Acid; copper hydroxide; sodium hydroxide In water; dimethyl sulfoxide at 120℃; for 6h; Inert atmosphere; Schlenk technique;95%
Stage #1: 4-iodoanisol With copper(l) iodide; 1,10-Phenanthroline; potassium hydroxide In water; dimethyl sulfoxide at 20 - 100℃; Inert atmosphere;
Stage #2: With hydrogenchloride In water; dimethyl sulfoxide at 20℃; Inert atmosphere;
94%
Stage #1: 4-iodoanisol With copper(l) iodide; 2-methyl-8-quinolinol; tetra(n-butyl)ammonium hydroxide In water; dimethyl sulfoxide at 100℃; for 10h;
Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide at 20℃;
94%
2-bromoanisole
578-57-4

2-bromoanisole

2-methoxy-phenol
90-05-1

2-methoxy-phenol

Conditions
ConditionsYield
With dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; boric acid; palladium diacetate; caesium carbonate In 1-methyl-pyrrolidin-2-one at 80℃; for 24h; Schlenk technique; Inert atmosphere;88%
Stage #1: 2-bromoanisole With copper(l) iodide; cesium hydroxide; 5-bromo-2-(1H-imidazol-2-yl)pyridine In water; dimethyl sulfoxide; tert-butyl alcohol at 120℃; for 36h; Inert atmosphere;
Stage #2: With hydrogenchloride In water; dimethyl sulfoxide; tert-butyl alcohol pH=1 - 2; Inert atmosphere;
83%
With tert.-butylhydroperoxide; n-butyllithium In tetrahydrofuran; hexane at 20℃; for 2h;78%
2-(2-methoxyphenoxy)-1-(4-methoxyphenyl)ethan-1-ol

2-(2-methoxyphenoxy)-1-(4-methoxyphenyl)ethan-1-ol

A

2-methoxy-phenol
90-05-1

2-methoxy-phenol

B

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With sodium tetrahydroborate; palladium on activated charcoal In water; ethyl acetate at 80℃; for 1h;A 95%
B 99%
With 5%-palladium/activated carbon; ammonium formate In water at 80℃; for 1h;A n/a
B 98%
With C32H25Cl2N6O2Rh2(1+)*Cl(1-); sodium hydroxide In water at 110℃; for 18h; Inert atmosphere;A 89%
B 86%
2-methoxyphenoxy-3',4'-dimethoxyacetophenone
22675-96-3

2-methoxyphenoxy-3',4'-dimethoxyacetophenone

A

2-methoxy-phenol
90-05-1

2-methoxy-phenol

B

Veratric acid
93-07-2

Veratric acid

Conditions
ConditionsYield
With oxygen; copper(II) nitrate In acetonitrile at 120℃; under 4500.45 Torr; for 10h;A n/a
B 99%
With sodium hydroxide for 2h; Reagent/catalyst; Time; Milling; Green chemistry;A 95 %Chromat.
B 80 %Chromat.
1-(4-methoxyphenyl)-3-hydroxy-2-(2-methoxyphenoxy)propan-1-one
92409-23-9

1-(4-methoxyphenyl)-3-hydroxy-2-(2-methoxyphenoxy)propan-1-one

A

2-methoxy-phenol
90-05-1

2-methoxy-phenol

B

3-hydroxy-1-(4-methoxyphenyl)-1-propan-1-one

3-hydroxy-1-(4-methoxyphenyl)-1-propan-1-one

Conditions
ConditionsYield
With formic acid; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 18h; Irradiation; Flow reactor; chemoselective reaction;A 94%
B 93%
With formic acid; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 24h; Inert atmosphere; Irradiation;A 82%
B 90%
With formic acid; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 15h; Irradiation; chemoselective reaction;A 88%
B 85%
With formic acid; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; N-ethyl-N,N-diisopropylamine In ethanol at 20℃; Irradiation; chemoselective reaction;A 56%
B 34%
With formic acid; 10-phenyl-10H-phenothiazine; N-ethyl-N,N-diisopropylamine In acetone at 20℃; for 96h; Inert atmosphere; Irradiation;A 28 mg
B 42 mg
1-(3,4-dimethoxyphenyl)-3-hydroxy-2-(2-methoxyphenoxy)propan-1-one
10548-77-3

1-(3,4-dimethoxyphenyl)-3-hydroxy-2-(2-methoxyphenoxy)propan-1-one

A

1-(3,4-dimethoxyphenyl)-3-hydroxypropan-1-one
104397-78-6

1-(3,4-dimethoxyphenyl)-3-hydroxypropan-1-one

B

2-methoxy-phenol
90-05-1

2-methoxy-phenol

Conditions
ConditionsYield
With formic acid; N-ethyl-N,N-diisopropylamine; Lumogen F Orange 240 In acetonitrile at 25℃; for 8h; Reagent/catalyst; UV-irradiation; Inert atmosphere;A 98%
B 97%
With formic acid; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 48h; Irradiation; chemoselective reaction;A 90%
B 95%
With formic acid; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 24h; Inert atmosphere; Irradiation;A 90%
B 80%
1-(benzyloxy)-2-methoxybenzene
835-79-0

1-(benzyloxy)-2-methoxybenzene

2-methoxy-phenol
90-05-1

2-methoxy-phenol

Conditions
ConditionsYield
With palladium diacetate; sodium hydride In N,N-dimethyl acetamide at 25℃; for 3h; Inert atmosphere;96%
With palladium diacetate; sodium hydride In N,N-dimethyl acetamide at 50℃; for 5h; Inert atmosphere;96%
With sulfosuccinic acid functionalized mesoporous silica In ethanol at 100℃;
1-(4-Hydroxyphenyl)-2-(2-methoxyphenoxy)-1-ethanol
106534-23-0

1-(4-Hydroxyphenyl)-2-(2-methoxyphenoxy)-1-ethanol

A

2-methoxy-phenol
90-05-1

2-methoxy-phenol

B

4-Hydroxyacetophenone
99-93-4

4-Hydroxyacetophenone

Conditions
ConditionsYield
With sodium tetrahydroborate; palladium on activated charcoal In water; ethyl acetate at 80℃; for 4h;A n/a
B 97%
With C32H25Cl2N6O2Rh2(1+)*Cl(1-); sodium hydroxide In water at 110℃; for 18h; Inert atmosphere;A 90%
B 76%
With C32H25Cl2N6O2Rh2(1+)*Cl(1-); sodium hydroxide In water at 110℃; for 18h; Inert atmosphere; Green chemistry;A 90%
B 76%
With C22H17Cl3N3ORh; sodium hydroxide In water for 60h; Inert atmosphere;
1-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)ethanol
7382-68-5

1-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)ethanol

A

2-methoxy-phenol
90-05-1

2-methoxy-phenol

B

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions
ConditionsYield
With sodium tetrahydroborate; palladium on activated charcoal In water; ethyl acetate at 80℃; for 14h;A n/a
B 96%
With C32H25Cl2N6O2Rh2(1+)*Cl(1-); sodium hydroxide In water at 110℃; for 18h; Inert atmosphere;A 86%
B 82%
With C32H25Cl2N6O2Rh2(1+)*Cl(1-); sodium hydroxide In water at 110℃; for 18h; Inert atmosphere; Green chemistry;A 86%
B 82%
With C22H17Cl3N3ORh; sodium hydroxide In water for 60h; Inert atmosphere;
1-methoxy-2-(methoxymethoxy)benzene
73220-26-5

1-methoxy-2-(methoxymethoxy)benzene

2-methoxy-phenol
90-05-1

2-methoxy-phenol

Conditions
ConditionsYield
With β‐cyclodextrin In water; acetone at 60℃; for 5.5h; Green chemistry;95%
With Montmorillonite K 10 In benzene at 50℃; for 1h;91%
With bismuth(III) chloride In water; acetonitrile at 50℃; for 1h; chemoselective reaction;83%
1-(3,4-dimethoxyphenyl)-3-hydroxy-2-(2-methoxyphenoxy)propan-1-one
10548-77-3

1-(3,4-dimethoxyphenyl)-3-hydroxy-2-(2-methoxyphenoxy)propan-1-one

A

2-methoxy-phenol
90-05-1

2-methoxy-phenol

B

Veratric acid
93-07-2

Veratric acid

Conditions
ConditionsYield
With dihydrogen peroxide; sodium hydroxide In tetrahydrofuran; methanol; water at 50℃; for 10h;A 45%
B 88%
With dihydrogen peroxide; sodium hydroxide In tetrahydrofuran; methanol at 50℃; for 10h;
With sodium hydroxide for 2h; Milling; Green chemistry;A 92 %Chromat.
B 70 %Chromat.
2-hydroxyphenyl boronic acid
89466-08-0

2-hydroxyphenyl boronic acid

2-methoxy-phenol
90-05-1

2-methoxy-phenol

Conditions
ConditionsYield
With oxygen; triethylamine In 2-methyltetrahydrofuran at 20℃; under 760.051 Torr; for 48h; UV-irradiation;69%
2-(2-methoxyphenoxy)-1-(4-methoxyphenyl)ethan-1-one
19513-80-5

2-(2-methoxyphenoxy)-1-(4-methoxyphenyl)ethan-1-one

A

2-methoxy-phenol
90-05-1

2-methoxy-phenol

B

4-methoxybenzoic acid
100-09-4

4-methoxybenzoic acid

Conditions
ConditionsYield
With oxygen; copper(II) nitrate In acetonitrile at 120℃; under 4500.45 Torr; for 10h;A n/a
B 99%
With oxygen; copper diacetate; triethylamine In dimethyl sulfoxide at 20℃; for 12h; Sealed tube;A 93%
B 83%
With water; oxalic acid at 100℃; for 24h; Reagent/catalyst;A 21 mg
B 73%
vanillin
121-33-5

vanillin

A

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

2-Methoxy-4-methylphenol

B

2-methoxy-phenol
90-05-1

2-methoxy-phenol

Conditions
ConditionsYield
With Ru/CNT; hydrogen In water; decalin at 200℃; under 7500.75 Torr; for 3h;
With hydrogen In water; decalin at 200℃; under 7500.75 Torr; for 6h; chemoselective reaction;
With formic acid In water at 130℃; for 6h; Reagent/catalyst; Green chemistry;A 69 %Chromat.
B 17 %Chromat.
2-Methoxyphenylboronic acid
5720-06-9

2-Methoxyphenylboronic acid

dihydrogen peroxide
7722-84-1

dihydrogen peroxide

2-methoxy-phenol
90-05-1

2-methoxy-phenol

Conditions
ConditionsYield
With ammonium bicarbonate In water at 20℃; for 2h; Schlenk technique;95%
3-methoxy-4-hydroxybenzoic acid
121-34-6

3-methoxy-4-hydroxybenzoic acid

2-methoxy-phenol
90-05-1

2-methoxy-phenol

Conditions
ConditionsYield
With cucumber juice at 30 - 35℃; for 48h; Inert atmosphere; Green chemistry;80%
With copper dichloride In water at 200℃; for 6h; Inert atmosphere; Autoclave;55%
decarboxylase
decarboxylase Enzymatic reaction;
With hydrogen In water at 170℃; under 7500.75 Torr; for 4h; Autoclave;
1-(benzyloxy)-2-methoxybenzene
835-79-0

1-(benzyloxy)-2-methoxybenzene

A

2-methoxy-phenol
90-05-1

2-methoxy-phenol

B

toluene
108-88-3

toluene

Conditions
ConditionsYield
With Ni7Au3; hydrogen In water at 130℃; under 7500.75 Torr; for 0.5h; Reagent/catalyst;A 44%
B 14%
With hydrogen In water at 60℃; under 7500.75 Torr; for 1h; Reagent/catalyst; Overall yield = 60 %Chromat.;
2-methoxyphenyl benzenesulfonate
3900-91-2

2-methoxyphenyl benzenesulfonate

2-methoxy-phenol
90-05-1

2-methoxy-phenol

Conditions
ConditionsYield
With potassium hydroxide In toluene; tert-butyl alcohol at 100℃; for 0.5h; Inert atmosphere;87%
2-Chloroanisole
766-51-8

2-Chloroanisole

2-methoxy-phenol
90-05-1

2-methoxy-phenol

Conditions
ConditionsYield
Stage #1: 2-Chloroanisole With tris-(dibenzylideneacetone)dipalladium(0); cesium hydroxide monohydrate; 2-((di-adamantan-1-yl)phosphaneyl)-1-(2,6-diisopropylphenyl)-1H-imidazole In 1,4-dioxane at 120℃; for 20h; Inert atmosphere;
Stage #2: With hydrogenchloride In 1,4-dioxane; water at 20℃; Inert atmosphere;
90%
With 2-di-tertbutylphosphino-3,4,5,6-tetramethyl-2',4',6'-triisopropyl-1,1'-biphenyl; potassium hydroxide; tris-(dibenzylideneacetone)dipalladium(0) In 1,4-dioxane; water at 100℃; for 24h;79%
With trans-di(μ-acetato)bis[o-(di-o-tolyl-phosphino)benzyl]dipalladium(II); C29H45Pt; potassium carbonate In water; N,N-dimethyl-formamide at 115℃; for 0.5h; Inert atmosphere; Microwave irradiation;60%
C20H24O6

C20H24O6

A

3-(3,4-dimethoxyphenyl)-1-propanol
3929-47-3

3-(3,4-dimethoxyphenyl)-1-propanol

B

4-propyl-1,2-dimethoxybenzene
5888-52-8

4-propyl-1,2-dimethoxybenzene

C

Acetic acid 3-(3,4-dimethoxy-phenyl)-propyl ester
100699-21-6

Acetic acid 3-(3,4-dimethoxy-phenyl)-propyl ester

D

2-methoxy-phenol
90-05-1

2-methoxy-phenol

Conditions
ConditionsYield
With palladium on activated charcoal; hydrogen; lanthanum(lll) triflate In 1,2-dichloro-ethane at 140℃; under 31029.7 Torr; for 16h;A 18%
B 32%
C 19%
D 69%
With palladium on activated charcoal; hydrogen; lanthanum(lll) triflate In 1,1,2,2-tetrachloroethane at 140℃; under 31029.7 Torr; for 2h;A 14%
B 7%
C 34%
D 59%
With palladium on activated charcoal; hydrogen; lanthanum(lll) triflate In 1,2-dichloro-ethane at 140℃; under 31029.7 Torr; for 16h;A 6%
B 11%
C 19%
D 56%
With palladium on activated charcoal; hydrogen; lanthanum(lll) triflate In 1,2-dichloro-ethane at 140℃; under 31029.7 Torr; for 16h;A 9%
B 17%
C 9%
D 43%
With palladium on activated charcoal; hydrogen; lanthanum(lll) triflate In 1,2-dichloro-ethane at 140℃; under 31029.7 Torr; for 16h;A 22%
B 12%
C 13%
D 13%
2-(2,6-dimethoxyphenoxy)-1-(3,4-dimethoxyphenyl)ethan-1-one
29389-04-6

2-(2,6-dimethoxyphenoxy)-1-(3,4-dimethoxyphenyl)ethan-1-one

A

β-oxo-β-(3,4-dimethoxyphenyl)-ethanol
37803-48-8

β-oxo-β-(3,4-dimethoxyphenyl)-ethanol

B

2-methoxy-phenol
90-05-1

2-methoxy-phenol

Conditions
ConditionsYield
With 1,10-Phenanthroline; oxygen; copper diacetate In methanol at 80℃; under 3000.3 Torr; for 3h;A 93%
B 21%
2-(2-methoxyphenoxy)-acetophenone
14385-48-9

2-(2-methoxyphenoxy)-acetophenone

A

1-phenyl-2-hydroxyethanone
582-24-1

1-phenyl-2-hydroxyethanone

B

2-methoxy-phenol
90-05-1

2-methoxy-phenol

Conditions
ConditionsYield
With 1,10-Phenanthroline; oxygen; copper diacetate In methanol at 80℃; under 3000.3 Torr; for 3h;A 95%
B 27%
2-(2-methoxyphenoxy)-1-(4-methoxyphenyl)ethan-1-one
19513-80-5

2-(2-methoxyphenoxy)-1-(4-methoxyphenyl)ethan-1-one

A

p-methoxybenzoylmethanol
4136-21-4

p-methoxybenzoylmethanol

B

2-methoxy-phenol
90-05-1

2-methoxy-phenol

Conditions
ConditionsYield
With 1,10-Phenanthroline; oxygen; copper diacetate In methanol at 80℃; under 3000.3 Torr; for 3h;A 85%
B 10%
C18H22O6

C18H22O6

A

2-methoxy-phenol
90-05-1

2-methoxy-phenol

B

1-(3,4-dimethoxyphenyl)ethanone
1131-62-0

1-(3,4-dimethoxyphenyl)ethanone

Conditions
ConditionsYield
With C32H25Cl2N6O2Rh2(1+)*Cl(1-); sodium hydroxide In water at 110℃; for 48h; Inert atmosphere;A 90%
B 85%
2-(2-methoxyphenoxy)-acetophenone
14385-48-9

2-(2-methoxyphenoxy)-acetophenone

di-n-propylamine
142-84-7

di-n-propylamine

A

N,N-dipropylbenzamide
14657-86-4

N,N-dipropylbenzamide

B

2-methoxy-phenol
90-05-1

2-methoxy-phenol

Conditions
ConditionsYield
With copper diacetate In dimethyl sulfoxide at 20℃; for 10h; Sealed tube;A 81%
B 91%
With copper(II) acetate monohydrate In dimethyl sulfoxide at 25℃; under 760.051 Torr; for 12h;A 46 %Chromat.
B 94 %Chromat.
2-(2-methoxyphenoxy)-1-(4-methoxyphenyl)ethan-1-one
19513-80-5

2-(2-methoxyphenoxy)-1-(4-methoxyphenyl)ethan-1-one

dimethyl amine
124-40-3

dimethyl amine

A

N,N-dimethyl-4-methoxybenzamide
7291-00-1

N,N-dimethyl-4-methoxybenzamide

B

2-methoxy-phenol
90-05-1

2-methoxy-phenol

Conditions
ConditionsYield
With copper diacetate In water; dimethyl sulfoxide at 20℃; for 12h; Sealed tube;A 78%
B 87%
With copper(II) acetate monohydrate In dimethyl sulfoxide at 25℃; under 760.051 Torr; for 9h;A 67 %Chromat.
B 86 %Chromat.
2-methoxyphenoxy-3',4'-dimethoxyacetophenone
22675-96-3

2-methoxyphenoxy-3',4'-dimethoxyacetophenone

dimethyl amine
124-40-3

dimethyl amine

A

3,4-dimethoxy-N,N-dimethylbenzamide
6967-45-9

3,4-dimethoxy-N,N-dimethylbenzamide

B

2-methoxy-phenol
90-05-1

2-methoxy-phenol

Conditions
ConditionsYield
With copper diacetate In water; dimethyl sulfoxide at 20℃; for 12h; Sealed tube;A 80%
B 76%
With copper(II) acetate monohydrate In dimethyl sulfoxide at 25℃; under 760.051 Torr; for 9h;A 80 %Chromat.
B 75 %Chromat.
4-bromoguaiacol
7368-78-7

4-bromoguaiacol

2-methoxy-phenol
90-05-1

2-methoxy-phenol

Conditions
ConditionsYield
Stage #1: 4-bromoguaiacol With nickel(II) iodide; 1,4-bis(dicyclohexylphosphino)butane; sodium carbonate; cesium iodide In tetrahydrofuran for 0.25h; Schlenk technique; Glovebox;
Stage #2: In tetrahydrofuran at 35℃; for 72h; Irradiation;
76%
2-Methoxyphenylboronic acid
5720-06-9

2-Methoxyphenylboronic acid

2-methoxy-phenol
90-05-1

2-methoxy-phenol

Conditions
ConditionsYield
With hydrazine hydrate; caesium carbonate at 80℃; for 8h;99%
With water; dihydrogen peroxide at 20℃; for 0.166667h; Green chemistry;97%
With water; caesium carbonate; hydrazine hydrate at 80℃; for 24h;97%
2-methoxy-phenol
90-05-1

2-methoxy-phenol

allyl bromide
106-95-6

allyl bromide

O-allyl guaiacol
4125-43-3

O-allyl guaiacol

Conditions
ConditionsYield
With potassium carbonate In acetone at 20℃; Reflux;100%
With potassium carbonate; potassium iodide In acetone for 18h; Reflux;100%
With potassium carbonate99%
2-methoxy-phenol
90-05-1

2-methoxy-phenol

4-bromoguaiacol
7368-78-7

4-bromoguaiacol

Conditions
ConditionsYield
With benzyltriphenylphosphonium peroxodisulfate; potassium bromide In acetonitrile for 4h; Heating;100%
With bromine In dichloromethane at -78 - -5℃; for 1h; Inert atmosphere;100%
With bromine In dichloromethane97%
methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

2-methoxy-phenol
90-05-1

2-methoxy-phenol

2-methoxyphenyl mesylate
98910-57-7

2-methoxyphenyl mesylate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0℃; for 2h; Inert atmosphere;100%
With triethylamine In ethyl acetate at 0 - 20℃; for 0.166667h; Green chemistry;97%
With triethylamine In dichloromethane at 20℃; for 1h; Inert atmosphere;97%
chloromethyl methyl ether
107-30-2

chloromethyl methyl ether

2-methoxy-phenol
90-05-1

2-methoxy-phenol

1-methoxy-2-(methoxymethoxy)benzene
73220-26-5

1-methoxy-2-(methoxymethoxy)benzene

Conditions
ConditionsYield
Stage #1: 2-methoxy-phenol With potassium tert-butylate In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 2h;
Stage #2: chloromethyl methyl ether In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 5h;
100%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃;99%
With N-ethyl-N,N-diisopropylamine at 0 - 20℃;99%
triethyl orthoacrylate
42216-96-6

triethyl orthoacrylate

2-methoxy-phenol
90-05-1

2-methoxy-phenol

2,2-diethoxy-8-methoxychroman
80515-77-1

2,2-diethoxy-8-methoxychroman

Conditions
ConditionsYield
With Trimethylacetic acid In toluene for 20h; Heating;100%
methanol
67-56-1

methanol

2-methoxy-phenol
90-05-1

2-methoxy-phenol

(+/-)-(1R,2R,7R,8S)-3,3,10,10-tetramethoxytricyclo[6.2.2.02,7]dodeca-5,11-diene-4,9-dione

(+/-)-(1R,2R,7R,8S)-3,3,10,10-tetramethoxytricyclo[6.2.2.02,7]dodeca-5,11-diene-4,9-dione

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene at 20℃;100%
With iodobenzene; 3-chloro-benzenecarboperoxoic acid at 25℃; for 0.166667h; Reagent/catalyst; Diels-Alder Cycloaddition;95%
With [bis(acetoxy)iodo]benzene at 0 - 20℃; for 1.5h;94%
2-methoxy-phenol
90-05-1

2-methoxy-phenol

benzenesulfonyl chloride
1939-99-7

benzenesulfonyl chloride

benzylsulfonylguaiacol
597581-23-2

benzylsulfonylguaiacol

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran100%
2-methoxy-phenol
90-05-1

2-methoxy-phenol

5-iodo-2-methoxyphenol
160257-85-2

5-iodo-2-methoxyphenol

Conditions
ConditionsYield
With iodine; n-butyltriphenylphosphonium peroxodisulfate In acetonitrile for 2h; Heating;100%
Multi-step reaction with 3 steps
1: 99 percent / pyridine / CH2Cl2 / 24 h / 0 - 18 °C
2: 73 percent / silver trifluoroacetate; iodine / CHCl3 / 5 h / 0 - 18 °C
3: 99 percent / potassium carbonate / methanol / 16 h / 18 °C
View Scheme
Multi-step reaction with 3 steps
1: 97 percent / DMAP; pyridine / CH2Cl2 / 1 h / 0 °C
2: ICl / CH2Cl2 / 168 h / 25 °C
3: 17.14 g / LiOH*H2O / methanol; tetrahydrofuran; H2O / 120 h / 25 °C
View Scheme
2-methoxy-phenol
90-05-1

2-methoxy-phenol

4-Fluoronitrobenzene
350-46-9

4-Fluoronitrobenzene

2-methoxyphenyl 4'-nitrophenyl ether
32795-85-0

2-methoxyphenyl 4'-nitrophenyl ether

Conditions
ConditionsYield
100%
With potassium carbonate In acetonitrile Heating;
With potassium carbonate In N,N-dimethyl-formamide for 8h; Inert atmosphere; Heating;
With potassium carbonate In N,N-dimethyl-formamide at 120℃;
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

2-methoxy-phenol
90-05-1

2-methoxy-phenol

2-methoxyphenyl triflate
59099-58-0

2-methoxyphenyl triflate

Conditions
ConditionsYield
With pyridine at 0 - 20℃; for 2h;100%
With pyridine In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere;98%
With pyridine In dichloromethane at 20℃; for 0.5h;96%
(S,S)-1-chloro-2,5-trans-diphenylphospholane
934421-88-2

(S,S)-1-chloro-2,5-trans-diphenylphospholane

2-methoxy-phenol
90-05-1

2-methoxy-phenol

(S,S)-1-(o-methoxyphenoxy)-2,5-trans-diphenylphospholane

(S,S)-1-(o-methoxyphenoxy)-2,5-trans-diphenylphospholane

Conditions
ConditionsYield
With lithium In diethyl ether at 20℃; for 3h;100%
2-Iodobenzyl bromide
40400-13-3

2-Iodobenzyl bromide

2-methoxy-phenol
90-05-1

2-methoxy-phenol

2-(2-iodobenzyloxy)-1-methoxybenzene
1332326-21-2

2-(2-iodobenzyloxy)-1-methoxybenzene

Conditions
ConditionsYield
With potassium carbonate In acetone at 50℃;100%
bromoacetic acid methyl ester
96-32-2

bromoacetic acid methyl ester

2-methoxy-phenol
90-05-1

2-methoxy-phenol

methyl (2-methoxyphenoxy) ethanoate
38768-62-6

methyl (2-methoxyphenoxy) ethanoate

Conditions
ConditionsYield
With potassium carbonate In acetone at 20℃; for 16h;100%
With potassium carbonate In acetone at 70℃; for 2h;34%
With potassium carbonate In tetrahydrofuran at 20 - 80℃;
2-methoxy-phenol
90-05-1

2-methoxy-phenol

ortho-nitrofluorobenzene
1493-27-2

ortho-nitrofluorobenzene

1-methoxy-2-(2-nitrophenoxy)benzene
74865-12-6

1-methoxy-2-(2-nitrophenoxy)benzene

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide at 95℃; for 20h;100%
With potassium carbonate In dimethyl sulfoxide at 95℃;
3-chloro-4-fluoronitrobenzene
350-30-1

3-chloro-4-fluoronitrobenzene

2-methoxy-phenol
90-05-1

2-methoxy-phenol

2-chloro-1-(2-methoxyphenoxy)-4-nitrobenzene
1097189-03-1

2-chloro-1-(2-methoxyphenoxy)-4-nitrobenzene

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 17h;100%
2-methoxy-phenol
90-05-1

2-methoxy-phenol

2,4-dideuterio-6-methoxy-phenol
7329-54-6

2,4-dideuterio-6-methoxy-phenol

Conditions
ConditionsYield
With perchloric acid; d(4)-methanol at 75℃; for 72h; Inert atmosphere;100%
2-methoxy-phenol
90-05-1

2-methoxy-phenol

cyclohexane
110-82-7

cyclohexane

Conditions
ConditionsYield
With hydrogen In dodecane at 200℃; under 15001.5 Torr; for 2h;99.6%
With rhodium contaminated with carbon; N-methyldiethanolamine trifluoromethanesulfonate; hydrogen at 120℃; under 30003 Torr; for 6h; Autoclave;93.5%
With Ni-doped silica; hydrogen In decalin at 140℃; under 22502.3 Torr; for 5h; Reagent/catalyst; Autoclave;91.7%
pivaloyl chloride
3282-30-2

pivaloyl chloride

2-methoxy-phenol
90-05-1

2-methoxy-phenol

2-methoxyphenyl pivalate
25491-51-4

2-methoxyphenyl pivalate

Conditions
ConditionsYield
In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere;99%
With pyridine
acetic anhydride
108-24-7

acetic anhydride

2-methoxy-phenol
90-05-1

2-methoxy-phenol

2-methoxyphenyl acetate
613-70-7

2-methoxyphenyl acetate

Conditions
ConditionsYield
With magnesium(II) perchlorate at 20℃; for 1h;99%
With iodine at 25℃; for 0.0166667h;99%
With Methylenediphosphonic acid at 20℃; for 2h; neat (no solvent);99%
N,N-diethylcarbamyl chloride
88-10-8

N,N-diethylcarbamyl chloride

2-methoxy-phenol
90-05-1

2-methoxy-phenol

N,N-diethyl-1-carbamyloxy-2-methoxybenzene
85630-19-9

N,N-diethyl-1-carbamyloxy-2-methoxybenzene

Conditions
ConditionsYield
With potassium carbonate In acetonitrile for 14h; Reflux;99%
With pyridine for 6h; Heating;96%
With sodium hydride In diethyl ether93%
2-Bromo-1-(3,4-dimethoxyphenyl)ethanone
1835-02-5

2-Bromo-1-(3,4-dimethoxyphenyl)ethanone

2-methoxy-phenol
90-05-1

2-methoxy-phenol

2-methoxyphenoxy-3',4'-dimethoxyacetophenone
22675-96-3

2-methoxyphenoxy-3',4'-dimethoxyacetophenone

Conditions
ConditionsYield
With potassium carbonate In acetone at 20℃; for 4h; Reflux;99%
With potassium carbonate In acetone97%
Stage #1: 2-methoxy-phenol With potassium carbonate In acetone at 20℃; for 0.5h;
Stage #2: 2-Bromo-1-(3,4-dimethoxyphenyl)ethanone In acetone Reflux;
95%
2-methoxy-phenol
90-05-1

2-methoxy-phenol

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

2-tosyloxyanisole
4416-67-5

2-tosyloxyanisole

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran; water at 0 - 20℃; for 2h; Reagent/catalyst; Green chemistry;99%
Stage #1: 2-methoxy-phenol With potassium hydroxide In tetrahydrofuran at 20℃; for 0.0833333h; Inert atmosphere;
Stage #2: p-toluenesulfonyl chloride In tetrahydrofuran at 60℃; Inert atmosphere;
99%
With triethylamine In dichloromethane at 20℃;99%
2-methoxy-phenol
90-05-1

2-methoxy-phenol

2-methoxycyclohexanol
2979-24-0

2-methoxycyclohexanol

Conditions
ConditionsYield
With 3 weight% Pd/C; hydrogen In Hexadecane at 249.84℃; under 22502.3 Torr; Reagent/catalyst; Autoclave;99%
With hydrogen In water at 80℃; under 15001.5 Torr; for 6.5h;99%
With Ni-doped silica; hydrogen In decalin at 140℃; under 22502.3 Torr; for 5h; Reagent/catalyst; Autoclave;95.5%
2-methoxy-phenol
90-05-1

2-methoxy-phenol

benzene-1,2-diol
120-80-9

benzene-1,2-diol

Conditions
ConditionsYield
Stage #1: 2-methoxy-phenol With pyridine; iodine; aluminium In acetonitrile for 18h; Reflux;
Stage #2: With hydrogenchloride In water; acetonitrile at 20℃;
99%
With hydrogenchloride In water at 250℃; under 37503.8 Torr; for 3h; Reagent/catalyst; Autoclave; Inert atmosphere; Green chemistry;97%
With aluminium(III) iodide; calcium oxide In acetonitrile at 80℃; for 18h; Reagent/catalyst;94%
2-methoxy-phenol
90-05-1

2-methoxy-phenol

cyclohexanol
108-93-0

cyclohexanol

Conditions
ConditionsYield
With hydrogen In water at 160℃; for 10h; Temperature; Concentration; Reagent/catalyst;99%
With potassium hydroxide; Raney Ni-Al; water at 90℃; for 16h;90.8%
With acetic acid; platinum Hydrogenation;
iodobenzene
591-50-4

iodobenzene

2-methoxy-phenol
90-05-1

2-methoxy-phenol

2-methoxyphenyl phenyl ether
1695-04-1

2-methoxyphenyl phenyl ether

Conditions
ConditionsYield
With copper(I) oxide; caesium carbonate; imidazole-4-carboxylic acid In acetonitrile at 80℃; for 24h;99%
With copper(l) iodide; 1-(dimethylamino-1-yl-pyridin-2-yl-methyl)naphthalen-2-ol; potassium carbonate In dimethyl sulfoxide at 120℃; for 24h; Ullmann Condensation; Green chemistry;99%
With potassium hydroxide In dimethyl sulfoxide at 110℃; for 15h; Inert atmosphere;96%
2-methoxy-phenol
90-05-1

2-methoxy-phenol

acetyl chloride
75-36-5

acetyl chloride

2-methoxyphenyl acetate
613-70-7

2-methoxyphenyl acetate

Conditions
ConditionsYield
99%
With pyridine In dichloromethane at 0 - 18℃; for 24h;99%
With pyridine In dichloromethane at 0 - 20℃; for 18h;99%

90-05-1Relevant articles and documents

Deposition–precipitation approach for preparing core/shell SiO2@Ni-Rh nanoparticles as an advanced catalyst for the dehydrogenation of 2-methoxycyclohexanol to guaiacol

Feng, Junbo,Jiang, Wei,Yuan, Caicai,Shi, Xiancai,Zang, Kai,Zhang, Yadong

, p. 106 - 113 (2018)

A novel core/shell nano-bimetallic catalyst SiO2@Ni-Rh was successfully prepared by deposition–precipitation method, using liquid ammonia as a precipitating agent. SEM, TEM, XRD, XPS, H2-TPR, H2-TPD and adsorption/desorption of nitrogen were employed to systematically investigate the surface morphology, size, chemical composition, reducibility, Ni dispersion and structure of the as-synthesized nanoparticles. It is found that the nickel and rhodium are uniformly dispersed on the silica surface to form core/shell SiO2@Ni-Rh nanoparticles with Ni atoms and Rh atoms as the outer shell and SiO2 as the core, which possess high dispersion of Ni on the surface and high specific surface area (234.063 m2/g) of the catalyst with the mean particle size of ca. 130 nm. The dehydrogenation of 2-methoxycyclohexanol to guaiacol was used as the model reaction for evaluating the catalytic activity of the as-synthesized core/shell various Ni and Rh-containing bimetallic nanoparticles in a tubular stainless steel reactor. SiO2@15Ni-0.4Rh nanoparticles have exhibited remarkable catalytic performance, with 98.3% conversion and 93.6% selectivity of guaiacol, due to high dispersion of metal nanoparticles and synergistic effect of bimetallic Ni-Rh over the special core/shell SiO2@Ni-Rh by the addition of rhodium. Furthermore, turn over frequency value of SiO2@15Ni-0.4Rh nanoparticles achieves 0.47 s?1, showing high catalytic efficiency. In general, the dehydrogenation of 2-methoxycyclohexanol over the core-shell-like SiO2@Ni-Rh nanoparticles in a continuous fixed-bed reactor is a more promising, high atom economy, high efficient, easy separation, environmental friendliness, green synthetic pathway of guaiacol.

-

Pearl

, p. 2196,2199 (1949)

-

-

Bamberger,Vischner

, p. 564 (1900)

-

Catechol O-methylation with dimethyl carbonate over different acid-base catalysts

Luque, Rafael,Manuel Campelo, Juan,Conesa, Tomas David,Luna, Diego,Marinas, Jose Maria,Romero, Antonio Angel

, p. 1228 - 1234 (2006)

A series of meso and microporous materials, previously described and characterised, were tested in the catechol O-alkylation process using methanol (MeOH) and dimethyl carbonate (DMC) as alkylating reagents. In this regard, interesting results in terms of catalytic activity and selectivity to the desired monomethylated product (guaiacol) compared to the dimethylated one (veratrole) were found for the majority of the catalysts. Moreover, DMC is a better methylating agent than methanol with respect to the conversion ratio of catechol and guaiacol. The presence of n-type nucleophilic centres (oxygen from the OH groups) together with π-type ones (aromatic ring) in catechol led only to O-alkylated (guaiacol and veratrole), whereas no C-alkylated products were found under the reaction conditions. AlPO4 and, especially, AlPO 4-Al2O3 systems showed the best performance in this alkylation process in comparison with silicoaluminophosphates (SAPO) and some acidic commercial zeolites (H-Y, H-β and H-ZSM-5). the Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2006.

-

Eisenbraun,Purves

, p. 2127 (1961)

-

Imidazolium-urea low transition temperature mixtures for the UHP-promoted oxidation of boron compounds

Martos, Mario,Pastor, Isidro M.

, (2022/01/03)

Different carboxy-functionalized imidazolium salts have been considered as components of low transition temperature mixtures (LTTMs) in combination with urea. Among them, a novel LTTM based on 1-(methoxycarbonyl)methyl-3-methylimidazolium chloride and urea has been prepared and characterized by differential scanning calorimetry throughout its entire composition range. This LTTM has been employed for the oxidation of boron reagents using urea-hydrogen peroxide adduct (UHP) as the oxidizer, thus avoiding the use of aqueous H2O2, which is dangerous to handle. This metal-free protocol affords the corresponding alcohols in good to quantitative yields in up to 5 mmol scale without the need of further purification. The broad composition range of the LTTM allows for the reaction to be carried out up to three consecutive times with a single imidazolium salt loading offering remarkable sustainability with an E-factor of 7.9, which can be reduced to 3.2 by the threefold reuse of the system.

One-Pot Transformation of Lignin and Lignin Model Compounds into Benzimidazoles

Guo, Tao,He, Jianghua,Liu, Tianwei,Zhang, Yuetao

supporting information, (2022/02/07)

It is a challenging task to simultaneously achieve selective depolymerization and valorization of lignin due to their complex structure and relatively stable bonds. We herein report an efficient depolymerization strategy that employs 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as oxidant/catalyst to selectively convert different oxidized lignin models to a wide variety of 2-phenylbenzimidazole-based compounds in up to 94 % yields, by reacting with o-phenylenediamines with varied substituents. This method could take full advantage of both Cβ and/or Cγ atom in lignin structure to furnish the desirable products instead of forming byproducts, thus exhibiting high atom economy. Furthermore, this strategy can effectively transform both the oxidized hardwood (birch) and softwood (pine) lignin into the corresponding degradation products in up to 45 wt% and 30 wt%, respectively. Through a “one-pot” process, we have successfully realized the oxidation/depolymerization/valorization of natural birch lignin at the same time and produced the benzimidazole derivatives in up to 67 wt% total yields.

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