Hydrochloric Acid → 4-(3-Oxobutyl)benzoic acid methyl ester
Reaction equation
[OH:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]([CH3:14])=[O:13])=[CH:6][CH:5]=1)=[O:3].Cl.[CH3:16]O>>[CH3:16][O:3][C:2]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]([CH3:14])=[O:13])=[CH:6][CH:5]=1)=[O:1]Participants
4
Procedure
Methyl 2-(4-hydroxycarbonylphenyl)ethyl ketone was esterified by reaction with methyl alcohol and hydrochloric acid to provide methyl 2-(4-methoxycarbonylphenyl)ethyl ketone. The ketone was condensed with optically active S-α-methylbenzylamine, and the imine which was formed was reduced to provide N-(α-methylbenzyl)-1-methyl-3-(4-methoxycarbonylphenyl)propylamine. The amine was converted to the hydrochloride salt, and fractional crystallization of the salt thus formed afforded optically active S-N-(α-methylbenzyl)-1-methyl-3-(4-methoxycarbonylphenyl)propylaminium chloride. M.P. 198°-205° C. [α]D -81.2° (MeOH).
Sources & evidence
- ORD record
- ord-c42d4df10eda45e1af0762ae927f5964
- Source dataset
- uspto-grants-1983_07
- Patent number
- US04391826
Reaction notes
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