Trimethylamine → alpha-Methoxyphenyl-hydroxy-cinnamic acid

HRID 918351

Reaction equation

HRID 918351 reaction equation
O[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1C=O.C[O:11][CH:12]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:13]([OH:15])=O.[C:22]([O:25]C(=O)C)(=[O:24])C.[CH3:29]N(C)C>>[CH3:29][O:15][C:13](=[C:12]([OH:11])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:2]1[CH:3]=[CH:6][CH:7]=[CH:8][CH:9]=1)[C:22]([OH:25])=[O:24]

Participants

5

Procedure

Hydroxybenzaldehyde is mixed with methoxyphenylacetic acid and the resulting mixture is reacted with acetic anhydride and trimethylamine, to obtain α-methoxyphenyl-hydroxy-cinnamic acid. When this compound is acetylated by heating in a nitrogen gas atmosphere in the presence of quinoline and copper chromite, acetoxy-methoxy-stilbene is formed. Then, this stilbene derivative is catalytically reduced and hydrolyzed with an alkali to obtain 3-hydroxy-5 -methoxybibenzyl.

Sources & evidence

ORD record
ord-076b9d2ad6ed4987ac3a79e2dc6df01e
Source dataset
uspto-grants-1976_07
Patent number
US03971651

Linked notes

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