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

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Reaction Steps

1.10 Gm. of 2-(5H-dibenzo[a,d]cyclohepten-2-yl)propionic acid is refluxed for 2 hours in 10 ml. of acetic acid and 7.5 ml. of water containing 2.24 gm. of ceric ammonium nitrate. The solution is poured into water and extracted with ethyl acetate. The extract is washed, dried and evaporated and the residue chromatographed on silica gel, eluting with 40:60:1 ethyl acetate:hexane:acetic acid, so as to isolate a 30% 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