Vanillin → Ferulic Acid

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH:9]=O)[CH:6]=[CH:5][C:4]=1[OH:11].[C:12]([O:15]C(=O)C)(=[O:14])[CH3:13]>>[C:12]([OH:15])(=[O:14])/[CH:13]=[CH:9]/[C:7]1[CH:6]=[CH:5][C:4]([OH:11])=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

Reactant 2

HCID 1183Vanillin

HCID 7918Acetic Anhydride

Product 1

HCID 445858Ferulic Acid

Procedure

Vaniline is reacted according to Perkin's reaction with acetic anhydride to form ferulic acid which is then decarbonized by heating to prepare 3-methoxy-4-hydroxystyrene. This compound is then acetylated with acetic anhydride, polymerized and then hydrolyzed to obtain 3-methoxy-4-hydroxystyrene polymer. ##STR4## wherein n stands for a positive number corresponding to the number of monomeric units in the polymer.

Sources & evidence

ORD record: ord-cc7e7a77387148e2acc9db9b074a2e1c
Source dataset: uspto-grants-1979_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04154653

Reaction notes

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