Methanol → 2-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl)propionic acid methyl ester

Participants

Reaction Steps

1.29 Gm. of 2-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl)propionitrile and 0.85 gm. of p-toluenesulfonic acid monohydrate are refluxed for six hours in 25 ml. of methanol. The solution is cooled and added to water and ether. The ethereal solution is washed, dried and evaporated to give a 75% yield of 2-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl)propionic acid methyl ester as an oil which slowly crystallized, m.p. 37°-39°C., NMR: δCDCl 3 1.55(d), 3.67(s), 3.83(g), 7.04(s) ppm. Use of 2-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl)acetonitrile gives a similar yield of 2-(5H-dibenzo[ a,d]cyclohepten-5-on-2-yl)acetic acid methyl ester, m.p. 67°-69°C.

Provenance & Evidence