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In a manner similar to that of W. S. Johnson and H. J. Glenn, J. Am. Chem. Soc., 71, 1092 (1949), the reaction of 3-(3-chloro[1,1'-biphenyl]-2-yl)propanoyl chloride (5.3 grams, 0.019 mole), aluminum chloride (3.33 grams, 0.025 mole) and benzene (125 ml) gave a brown oil. The oil was subjected to column chromatography on silica gel and eluted with 9:1 chloroform:petroleum ether to give 8-chloro-6,7-dihydro-5H-dibenzo[a,c]cycloheptene-5-one as a solid.

1. customgave a brown oil
2. washeluted with 9:1 chloroform