Vanillin → 3,4,5-Trimethoxybenzaldehyde

HRID 462135Notes

Reaction equation

HRID 462135 reaction equation
[OH:1][C:2]1C(O)=C(OC)C=C(C=1)C=O.[O:13]=[CH:14][C:15]1[CH:23]=[CH:22][C:20]([OH:21])=[C:17]([O:18][CH3:19])[CH:16]=1.S(OC)(O[CH3:28])(=O)=O.C(=O)([O-])[O-]>CC(C)=O>[CH3:19][O:18][C:17]1[CH:16]=[C:15]([CH:23]=[C:22]([O:1][CH3:2])[C:20]=1[O:21][CH3:28])[CH:14]=[O:13]

Participants

6

Reactant 4

HCID 1183VanillinHCID 6497Dimethyl SulfateHCID 19660Carbonate IonHCID 775353,4-Dihydroxy-5-methoxybenzaldehyde

Product 1

HCID 68583,4,5-Trimethoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

U.S. Pat. No. 3,855,306 discloses methylation of 5-hydroxyvanillin (initially prepared from vanillin by bromination and subsequent hydrolysis) with dimethyl sulfate in the presence of an alkali carbonate in an organic medium such as acetone. 3,4,5,-Trimethoxybenzaldehyde in yields of about 94% are obtained in this method, but the reaction is slow and operating with organic solvents presents disadvantages of operation and cost.

Sources & evidence

ORD record
ord-e86a3e895a804610b62313758ada17e7
Source dataset
uspto-grants-1977_12
Patent number
US04065504

Reaction notes

Loading…