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 6 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: δCDCl3 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