Veratrole → 4-(3,4-Dimethoxyphenyl)-4-oxobutanoic acid

HRID 483358Notes

Reaction equation

HRID 483358 reaction equation
C(CC1SC(S)=NC=1)(O)=O.[C:11]1([O:19][CH3:20])[C:12](=[CH:15][CH:16]=[CH:17][CH:18]=1)[O:13][CH3:14].[C:21]1(=[O:27])[O:26][C:24](=[O:25])[CH2:23][CH2:22]1.[Cl-].[Al+3].[Cl-].[Cl-]>>[CH3:14][O:13][C:12]1[CH:15]=[C:16]([CH:17]=[CH:18][C:11]=1[O:19][CH3:20])[C:21]([CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[O:27]

Participants

5

Reactant 4

HCID 7043VeratroleHCID 7922Succinic anhydrideHCID 6451240Aluminum(III) ChlorideHCID 178525224HCID 178525224, compound

Product 1

HCID 2193904-(3,4-Dimethoxyphenyl)-4-oxobutanoic acid

Procedure

A 5-carboxymethyl-2-mercaptothiazole derivative can be prepared by reacting veratrole with succinic anhydride in the presence of anhydrous aluminum chloride to obtain 3-(3,4-dimethoxybenzoyl)propionic acid, subjecting the compound to demethylation with hydrobromic acid to obtain 3-(3,4-dihydroxybenzoyl)propionic acid, subjecting the compound to enol-lactonation in the presence of acetic anhydride and sodium acetate, reacting the resulting compound sequentially with N-bromosuccinimide and with diphenyldiazomethane to obtain 3-(3,4-diacetoxybenzoyl)-3-bromopropionate, and further reacting the compound with ammonium dithiocarbamate.

Sources & evidence

ORD record
ord-377fb88fc1d74706aa4d3e0f1ef7bf32
Source dataset
uspto-grants-1993_07
Patent number
US05225406

Reaction notes

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