Production Method 1

91-16-7

93-51-6

59056-76-7

5888-52-8

874-41-9

Reaction Conditions

1.1 Reagents: Lithium borohydride Solvents: Tetrahydrofuran ;  0 °C; 0 °C → rt; overnight, rt
1.2 Reagents: Water ;  rt
2.1 Reagents: Sodium hydroxide Solvents: Ethanol ;  6 h, 330 °C

Reference

Molybdenum carbide, supercritical ethanol and base: Keys for unlocking renewable BTEX from lignin

Lui, Matthew Y.; et al, Applied Catalysis, 2023, 325,

Production Method 2

91-16-7

Reaction Conditions

1.1 Reagents: Water Catalysts: [1,1,1-Trifluoro-N-[(trifluoromethyl)sulfonyl]methanesulfonamidato-κN](triphenyl… Solvents: Dimethyl carbonate ;  1.5 h, 70 °C

Reference

Gold-Catalyzed Proto- and Deuterodeboronation

Barker, Graeme; Webster, Stacey; Johnson, David G.; Curley, Rachel; Andrews, Matthew; et al, Journal of Organic Chemistry, 2015, 80(20), 9807-9816

Production Method 3

90-05-1

91-16-7

Reaction Conditions

1.1 Catalysts: 1-Ethyl-3-methylimidazolium bromide ;  rt; rt → 120 °C; 1.8 h, 120 °C

Reference

Catalytic O-methylation of phenols with dimethyl carbonate to aryl methyl ethers using [BMIm]Cl

Shen, Zhen Lu; Jiang, Xuan Zhen; Mo, Wei Min; Hu, Bao Xiang; Sun, Nan, Green Chemistry, 2005, 7(2), 97-99

Production Method 4

141077-52-3

91-16-7

Reaction Conditions

1.1 Reagents: Methanol ,  Ammonium acetate ,  Magnesium Catalysts: Palladium Solvents: Methanol ;  1 h, 20 °C

Reference

Mechanistic study of a Pd/C-catalyzed reduction of aryl sulfonates using the Mg-MeOH-NH4OAc system

Mori, Akinori; Mizusaki, Tomoteru; Ikawa, Takashi; Maegawa, Tomohiro; Monguchi, Yasunari; et al, Chemistry - A European Journal, 2007, 13(5), 1432-1441

Production Method 5

91-16-7

Reaction Conditions

1.1 Catalysts: 1,8-Diazabicyclo[5.4.0]undec-7-ene Solvents: Acetonitrile ;  40 min, 170 °C

Reference

Microwave-assisted methylation of dihydroxybenzene derivatives with dimethyl carbonate

Lui, Matthew Y.; Lokare, Kapil S.; Hemming, Ellen; Stanley, Jessica N. G.; Perosa, Alvise; et al, RSC Advances, 2016, 6(63), 58443-58451

Production Method 6

91-16-7

Reaction Conditions

1.1 Reagents: Cesium carbonate Catalysts: Dimethylglycine hydrochloride ,  Cuprous iodide ;  24 h, 100 °C

Reference

N,N-Dimethylglycine-promoted Ullmann-type coupling reactions of aryl iodides with aliphatic alcohols

Zhang, Hui; Ma, Dawei; Cao, Weiguo, Synlett, 2007, (2), 243-246

Production Method 7

91-16-7

93-51-6

59056-76-7

5888-52-8

874-41-9

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Ethanol ;  6 h, 330 °C

Reference

Molybdenum carbide, supercritical ethanol and base: Keys for unlocking renewable BTEX from lignin

Lui, Matthew Y.; et al, Applied Catalysis, 2023, 325,

Production Method 8

13078-21-2

91-16-7

93-51-6

59056-76-7

5888-52-8

874-41-9

Reaction Conditions

1.1 Reagents: Lithium diisopropylamide Solvents: Tetrahydrofuran ;  1 h, -78 °C; 10 min
1.2 Solvents: Tetrahydrofuran ;  30 min; 2 h
1.3 Reagents: Carbon dioxide
2.1 Reagents: Lithium borohydride Solvents: Tetrahydrofuran ;  0 °C; 0 °C → rt; overnight, rt
2.2 Reagents: Water ;  rt
3.1 Reagents: Sodium hydroxide Solvents: Ethanol ;  6 h, 330 °C

Reference

Molybdenum carbide, supercritical ethanol and base: Keys for unlocking renewable BTEX from lignin

Lui, Matthew Y.; et al, Applied Catalysis, 2023, 325,

Production Method 9

90-05-1

105-36-2

91-16-7

93-51-6

59056-76-7

5888-52-8

874-41-9

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Acetone ;  overnight, rt → reflux
2.1 Reagents: Lithium diisopropylamide Solvents: Tetrahydrofuran ;  1 h, -78 °C; 10 min
2.2 Solvents: Tetrahydrofuran ;  30 min; 2 h
2.3 Reagents: Carbon dioxide
3.1 Reagents: Lithium borohydride Solvents: Tetrahydrofuran ;  0 °C; 0 °C → rt; overnight, rt
3.2 Reagents: Water ;  rt
4.1 Reagents: Sodium hydroxide Solvents: Ethanol ;  6 h, 330 °C

Reference

Molybdenum carbide, supercritical ethanol and base: Keys for unlocking renewable BTEX from lignin

Lui, Matthew Y.; et al, Applied Catalysis, 2023, 325,

Production Method 10

8068-05-1

91-16-7

496-16-2

876-02-8

90-00-6

93-51-6

608-43-5

39151-19-4

6443-69-2

90-05-1

96-39-9

2758-18-1

105-38-4

27129-87-9

Reaction Conditions

1.1 250 h

Reference

Catalytic pyrolysis of lignin over hierarchical HZSM 5 zeolites prepared by post-treatment with alkaline solutions

Tang, Songshan; et al, Journal of Analytical and Applied Pyrolysis, 2019, 137, 86-95

Production Method 11

90-05-1

91-16-7

Reaction Conditions

1.1 Catalysts: Dimethyl sulfide Solvents: Dimethyl carbonate ;  4 h, rt → 220 °C

Reference

Methylation with Dimethyl Carbonate/Dimethyl Sulfide Mixtures: An Integrated Process without Addition of Acid/Base and Formation of Residual Salts

Lui, Yuen Wai; Chan, Bun ; Lui, Matthew Y., ChemSusChem, 2022, 15(3),

Production Method 12

91-16-7

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Dimethylformamide ;  18 h, rt

Reference

Strain-Promoted Double Azide Addition to Octadehydrodibenzo[12]annulene Derivatives

Fukushima, Satomi; Ashizawa, Minoru; Kawauchi, Susumu; Michinobu, Tsuyoshi, Helvetica Chimica Acta, 2019, 102(4),

Production Method 13

90-05-1

91-16-7

Reaction Conditions

1.1 Catalysts: 1H-Imidazolium, 2-carboxy-1,3-dimethyl-, inner salt Solvents: Acetonitrile ;  80 min, 160 °C

Reference

Masked N-Heterocyclic Carbene-Catalyzed Alkylation of Phenols with Organic Carbonates

Lui, Matthew Y. ; Yuen, Alexander K. L.; Masters, Anthony F.; Maschmeyer, Thomas, ChemSusChem, 2016, 9(17), 2312-2316

Production Method 14

141077-52-3

91-16-7

Reaction Conditions

1.1 Reagents: Ammonium acetate ,  Magnesium Catalysts: Palladium Solvents: Methanol ;  1 h, 20 °C

Reference

Pd/C-Catalyzed Deoxygenation of Phenol Derivatives Using Mg Metal and MeOH in the Presence of NH4OAc

Sajiki, Hironao; Mori, Akinori; Mizusaki, Tomoteru; Ikawa, Takashi; Maegawa, Tomohiro; et al, Organic Letters, 2006, 8(5), 987-990

Production Method 15

91-16-7

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Acetone ;  10 min, rt
1.2 1.5 h, rt; overnight, 60 °C

Reference

2,1,3-Benzoxadiazole and 2,1,3-benzothiadiazole-based fluorescent compounds: Synthesis, characterization and photophysical/electrochemical properties

Behramand, Behramand; Molin, Fernando; Gallardo, Hugo, Dyes and Pigments, 2012, 95(3), 600-605

Production Method 16

91-16-7

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Water ;  rt → 10 °C; < 10 °C
1.2 < 10 °C; < 10 °C → 80 °C; 0.5 h, 80 °C; 80 °C → 50 °C; 50 °C → 80 °C; 0.5 h, 80 °C; 80 °C → 50 °C; 50 °C → 80 °C; 3 h, 80 °C

Reference

Synthesis of 3,4-dimethoxybenzaldehyde through Vilsmeier-reaction

Wang, Chengfeng; Lin, Yuanbin, Changsha Dianli Xueyuan Xuebao, 2004, 19(4), 87-88

Production Method 17

635-67-6

91-16-7

Reaction Conditions

1.1 Reagents: Hexamethylphosphoramide ,  Sodium hydride Solvents: Tetrahydrofuran

Reference

A facile and direct conversion of aryl acetate to alkyl aryl ether

Yamashita, A.; Toy, A., Synthetic Communications, 1989, 19(5-6), 755-61

Veratrole Raw materials

• Methanesulfonic acid, trifluoro-, 3,4-dimethoxyphenyl ester
• 1,2-Diacetoxybenzene
• Guaiacol
• Ethyl 2-(2-methoxyphenoxy)acetate
• Sulfate Lignin
• Ethyl bromoacetate

Veratrole Preparation Products

• Coumaran (496-16-2)
• 4'-Hydroxy-3'-methylacetophenone (876-02-8)
• 2-Ethylphenol (90-00-6)
• 2-Methoxy-4-methylphenol (93-51-6)
• 2,3-Xylohydroquinone (608-43-5)
• 3′,5′-Dimethoxyacetophenone (39151-19-4)
• 3,4,5-Trimethoxytoluene (6443-69-2)
• Guaiacol (90-05-1)
• Benzene, 4-butyl-1,2-dimethoxy- (59056-76-7)
• 1,2-Dimethoxy-4-propylbenzene (5888-52-8)
• 1-methylcyclopenta-1,3-diene (96-39-9)
• 1-Ethyl-2,4-dimethylbenzene (874-41-9)
• 3-methylcyclopent-2-en-1-one (2758-18-1)
• Vinyl Propionate (stabilized with MEHQ) (105-38-4)
• 3,5-Dimethylbenzyl alcohol (27129-87-9)

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• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Dimethoxybenzenes
• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Methoxybenzenes Dimethoxybenzenes
• Solvents and Organic Chemicals Organic Compounds Alcohol/Ether

• 26638-03-9(Phenol, methoxy-)
• 126840-15-1(1,2-Dimethoxybenzene-3,4,5,6-d4)
• 90-05-1(Guaiacol)
• 7329-52-4(2-Methoxyphenol-3,4,5,6-d4)
• 203645-56-1(1,2-dimethoxybenzene-4,5-d2)
• 20189-11-1(2-Methoxyphenol-3,4,5,6-d4,OD)
• 24658-24-0(Catechol Dimethylether-d6)
• 1065473-05-3(2-Methoxy-D3-phenol-3,4,5,6-D4)
• 74495-69-5(2-Methoxyphenol-d3)
• 9009-62-5(2-Methyloxyphenol)