HCID 13191786, compound → HCID 13191789, compound

Participants

Reaction Steps

By use of the methods described in Example 3,3-bromo-4'-methyl benzophenone (Ipatieff and Friedman, J. Amer. Chem. Soc., 1939, 61, 684) was converted into ethyl 3-(4-toluoyl)cinnamate, m.p. 86°-87°, and thence into a mixture of the (E)- and (Z)-isomers of ethyl 3-(3-dimethylamino-1-(4-tolyl)prop-1-enyl)cinnamate. Hydrolysis of this ester mixture and separation of the mixture of carboxylic acids by crystallization yielded (E)-3-(3-dimethylamino-1-(4-tolyl)prop-1E-enyl)cinnamic acid, m.p. 200°-205° C., and (E)-3-(3-dimethylamino-1-(4-tolyl)prop-1Z-enyl)cinnamic acid, m.p. 200°-205° C.

Provenance & Evidence