2,2-Diethylpropanedioate → 4-Acetyl-3,5-dimethoxybenzoic acid
Reaction equation
[CH3:1]OC1C=C(C=C(OC)C=1CC)C(Cl)=O.[C:16]([C:20]1[CH:28]=[C:27]([O:29][CH3:30])[C:23]([C:24](Cl)=[O:25])=[C:22]([O:31][CH3:32])[CH:21]=1)([O:18]C)=[O:17].C(C(CC)(C([O-])=O)C([O-])=O)C>>[C:24]([C:23]1[C:27]([O:29][CH3:30])=[CH:28][C:20]([C:16]([OH:18])=[O:17])=[CH:21][C:22]=1[O:31][CH3:32])(=[O:25])[CH3:1]Participants
Procedure
3,5-Dimethoxy-4-ethyl-benzoyl chloride. Starting from 4-carbomethoxy-2,6-dimethoxy-benzoyl chloride and diethyl-malonate, and following the procedure described by H. G. Walker et al., in Journal Am.Chem.Soc., 68, 1387 (1946), the methyl ester of 4-acetyl-3,5-dimethoxy-benzoic acid is obtained, m.p. 100°-102°C. This compound is hydrolized under alkaline conditions to the corresponding acid. (M.p. 174°-179°C from ethanol/water). The conversion of the -COCH3 group at the position 4 to --CH2CH3 is achieved by the reductive method described by Huang Minlon in Journal Am.Chem.Soc., 68, 2487, 1946. The obtained 3,5-dimethoxy-4-ethylbenzoic acid has m.p. 190°-91°C (from methanol/water). The corresponding chloride is obtained in the same way as for the compound under A). M.p. 88°-89°C (from diethyl ether).
Sources & evidence
- ORD record
- ord-08ae3c99769d4ba6bcaac90a89df9c3c
- Source dataset
- uspto-grants-1976_08
- Patent number
- US03978065
Reaction notes
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