Production Method 1

1521-38-6

877-22-5

Reaction Conditions

1.1 Reagents: Boron trichloride

Reference

Boron trichloride as a selective demethylating agent

Dean, F. M.; et al, Tetrahedron Letters, 1966, (35), 4153-9

Production Method 2

586-38-9

877-22-5

Reaction Conditions

1.1 Reagents: Piperidine, 2,2,6,6-tetramethyl-, lithium salt (1:1) Solvents: Tetrahydrofuran ;  0 °C; 2 h, 0 °C
1.2 Reagents: Oxygen ;  30 min, 0 °C; 2 h, 40 - 65 °C

Reference

First General, Direct, and Regioselective Synthesis of Substituted Methoxybenzoic Acids by Ortho Metalation

Nguyen, Thi-Huu; et al, Journal of Organic Chemistry, 2007, 72(9), 3419-3429

Production Method 3

586-38-9

877-22-5

Reaction Conditions

1.1 Reagents: Butyllithium ,  2,2,6,6-Tetramethylpiperidine ,  Oxygen Solvents: Tetrahydrofuran ,  Hexane
1.2 Solvents: Water

Reference

Reactions of regioselective metalation of unprotected alkoxybenzoic acids. Scopes, limitations and mechanism

Nguyen, Thi Huu, 2006, , ,

Production Method 4

41799-27-3

877-22-5

Reaction Conditions

1.1 Reagents: Disodium phosphate ,  Monopotassium phosphate ,  Oxygen ,  Ammonium sulfate ,  Magnesium chloride ,  Calcium nitrate Solvents: Water ;  28 °C; pH 2.0

Reference

Metabolism of hydroxydibenzofurans, methoxydibenzofurans, acetoxydibenzofurans, and nitrodibenzofurans by Sphingomonas sp. strain HH69

Harms, Hauke; et al, Applied and Environmental Microbiology, 1995, 61(7), 2499-505

Production Method 5

19261-06-4

877-22-5

Reaction Conditions

1.1 -
2.1 Reagents: Disodium phosphate ,  Monopotassium phosphate ,  Oxygen ,  Ammonium sulfate ,  Magnesium chloride ,  Calcium nitrate Solvents: Water ;  28 °C; pH 2.0

Reference

Metabolism of hydroxydibenzofurans, methoxydibenzofurans, acetoxydibenzofurans, and nitrodibenzofurans by Sphingomonas sp. strain HH69

Harms, Hauke; et al, Applied and Environmental Microbiology, 1995, 61(7), 2499-505

Production Method 6

90-05-1

877-22-5

2169-28-0

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran
1.2 -

Reference

Dianion metalation reactions of N,N-dimethylvanillylamine and N,N-dimethylisovanillylamine

Hlasta, Dennis J.; et al, Tetrahedron Letters, 1985, 26(18), 2151-4

Production Method 7

57543-87-0

877-22-5

65-85-0

88252-61-3

Reaction Conditions

1.1 Reagents: Potassium superoxide Solvents: Dimethyl sulfoxide

Reference

Reaction of potassium superoxide with 3-nitro-2-phenyl-2H-1-benzopyrans and their dihydro derivatives

Rao, Takkellapati Sudhakar; et al, Heterocycles, 1987, 26(8), 2117-24

Production Method 8

148-53-8

877-22-5

Reaction Conditions

1.1 Reagents: Potassium hydroxide ,  Oxygen ,  Sodium borohydride Catalysts: Palladium Solvents: Methanol ,  Water ;  48 h, rt; rt; rt
1.2 Reagents: Hydrochloric acid Solvents: Water ;  neutralized, rt

Reference

Environmentally benign oxidation reaction of aldehydes to their corresponding carboxylic acids using Pd/C with NaBH4 and KOH

Lim, Minkyung; et al, Tetrahedron Letters, 2007, 48(22), 3835-3839

Production Method 9

148-53-8

877-22-5

Reaction Conditions

1.1 Reagents: Potassium hydroxide Solvents: Water ;  20 min, rt; 1 h, 155 - 160 °C

Reference

Facile synthesis, isolation and characterization of 1-(4-hydroxy-3-methoxyphenyl)ethanone (acetovanillone) and its isomeric related substances as key starting materials for an antipsychotic drug: iloperidone

Boodida, S. ; et al, Asian Journal of Chemistry, 2022, 34(5), 1245-1254

Production Method 10

1521-38-6

877-22-5

Reaction Conditions

1.1 Reagents: Piperazine Solvents: Dimethylacetamide
1.2 Reagents: Hydrochloric acid Solvents: Water

Reference

Regioselective dealkylation of 2-alkoxybenzoic acid and its amide derivatives with aliphatic amines

Nishioka, Hiroyasu; et al, Synthesis, 2000, (2), 243-246

Production Method 11

4383-05-5

877-22-5

Reaction Conditions

1.1 Reagents: Potassium hydroxide ,  Oxygen ,  Sodium borohydride Catalysts: Palladium Solvents: Methanol ,  Water ;  2 - 36 h, rt

Reference

Pd/C and NaBH4 in basic aqueous alcohol: an efficient system for an environmentally benign oxidation of alcohols

An, Gwangil; et al, Synthesis, 2010, (3), 477-485

Production Method 12

126431-96-7

877-22-5

Reaction Conditions

Reference

Secoiridoids and a phenolic glucoside from Gentiana pyrenaica

Garcia, Julian; et al, Journal of Natural Products, 1989, 52(5), 996-1002

Production Method 13

101762-27-0

877-22-5

Reaction Conditions

1.1 Reagents: Disodium phosphate ,  Monopotassium phosphate ,  Oxygen ,  Ammonium sulfate ,  Magnesium chloride ,  Calcium nitrate Solvents: Water ;  28 °C; pH 2.0
2.1 -
3.1 Reagents: Disodium phosphate ,  Monopotassium phosphate ,  Oxygen ,  Ammonium sulfate ,  Magnesium chloride ,  Calcium nitrate Solvents: Water ;  28 °C; pH 2.0

Reference

Metabolism of hydroxydibenzofurans, methoxydibenzofurans, acetoxydibenzofurans, and nitrodibenzofurans by Sphingomonas sp. strain HH69

Harms, Hauke; et al, Applied and Environmental Microbiology, 1995, 61(7), 2499-505

Production Method 14

132-64-9

877-22-5

Reaction Conditions

1.1 -
2.1 -
3.1 Reagents: Disodium phosphate ,  Monopotassium phosphate ,  Oxygen ,  Ammonium sulfate ,  Magnesium chloride ,  Calcium nitrate Solvents: Water ;  28 °C; pH 2.0

Reference

Metabolism of hydroxydibenzofurans, methoxydibenzofurans, acetoxydibenzofurans, and nitrodibenzofurans by Sphingomonas sp. strain HH69

Harms, Hauke; et al, Applied and Environmental Microbiology, 1995, 61(7), 2499-505

Production Method 15

57544-05-5

877-22-5

100-09-4

91735-21-6

Reaction Conditions

1.1 Reagents: Potassium superoxide Solvents: Dimethyl sulfoxide

Reference

Reaction of potassium superoxide with 3-nitro-2-phenyl-2H-1-benzopyrans and their dihydro derivatives

Rao, Takkellapati Sudhakar; et al, Heterocycles, 1987, 26(8), 2117-24

o-Vanillic Acid Raw materials

• Dibenzofuran
• b-D-Glucopyranose,1-[(2R)-3-[(3,4-dimethoxybenzoyl)oxy]-2-methylpropanoate]6-(4-hydroxy-3-methoxybenzoate) (9CI)
• Guaiacol
• 8-methoxy-2-(4-methoxyphenyl)-3-nitro-2H-chromene
• 8-oxatricyclo7.4.0.0,2,7trideca-1(9),2(7),3,5,10,12-hexaen-6-ol
• 2,3-Dimethoxybenzoic acid
• Acetic Acid;dibenzofuran-4-ol
• 3-Methoxybenzoic acid
• 2-Hydroxy-3-methoxybenzyl alcohol
• 1-Methoxydibenzofuran
• 8-methoxy-3-nitro-2-phenyl-2H-chromene
• 2-Hydroxy-3-methoxybenzaldehyde

o-Vanillic Acid Preparation Products

• o-Vanillic Acid (877-22-5)
• p-Anisic acid (100-09-4)
• Benzoic acid (65-85-0)
• 4H-1-Benzopyran-4-one, 3-hydroxy-8-methoxy-2-(4-methoxyphenyl)- (91735-21-6)
• 3-hydroxy-2-methoxybenzoic acid (2169-28-0)
• 4H-1-Benzopyran-4-one, 3-hydroxy-8-methoxy-2-phenyl- (88252-61-3)

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• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives M-methoxybenzoic acids and derivatives

• 3507-08-2(5-Carboxyvanillin)
• 50855-25-9(Benzoic acid, trimethoxy-)
• 5653-56-5(Benzoic acid, 2,3-dimethoxy-5-methyl-)
• 1521-38-6(2,3-Dimethoxybenzoic acid)
• 5653-46-3(2-Hydroxy-3,4-dimethoxybenzoic acid)
• 77869-39-7(Benzoic acid, 2,3-dimethoxy-4-methyl-)
• 118303-91-6(Benzoic acid,3,6-dihydroxy-2-methoxy-)
• 2169-28-0(3-hydroxy-2-methoxybenzoic acid)
• 3934-81-4(2,3-Dihydroxy-4-methoxybenzoic Acid)
• 2134-91-0(5-Carboxyvanillic Acid)