Water → 5H-Dibenzo(a,d)cycloheptene-2-acetic acid, alpha-methyl-5-oxo-

Participants

Reaction Conditions

Reaction Steps

1.0 Gm. of silver p-toluenesulfonate and 0.5 gm. of 2-(5-bromo-5H-dibenzo[a,d]cyclohepten-2-yl)propionic acid are stirred in 50 ml. of acetonitrile in the dark for 6 hours. Water, ether and 2.0 ml. of acetic acid are added. The ethereal layer is washed, dried and evaporated. The products, 2-(5-p-toluene-sulfonyloxy-5H-dibenzo[a,d]cyclohepten-2-yl)propionic acid, is dissolved in 10 ml. of dimethylsulfoxide and heated to 120° C. for 5 minutes, then cooled, poured into water and extracted with ethyl acetate. The solution is washed, dried and evaporated. The residue is chromatographed on silica gel, eluting with 40:60:1 ethyl acetate: acetic acid, so as to isolate a 15% yield of 2-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl propionic acid, m.p. (chloroform-hexane) 138°-139° C.; m.p. (acetone-hexane) 113°-115° C.

Provenance & Evidence