Thionyl Chloride → o-(2',5'-Dimethylbenzoylvinyl)benzoyl chloride

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Reaction Steps

A 1 liter flask was charged with 32.2 grams (115 mmol) of 3-(2',5'-dimethylphenacyl)phthalide, 200 ml of benzene and 50 ml of thionyl chloride. After heating at reflux on a steambath for 30 minutes, the solution was concentrated. The residue was triturated with ligroin to give 32.5 grams of o-(2',5'-dimethylbenzoylvinyl)benzoyl chloride, m.p. 96°-98° C. Analysis shows 72.29% carbon, 5.07% hydrogen and 11.80% chlorine as against calculated values of 72.36%, 5.06% and 11.87% for C18H15ClO2.

Provenance & Evidence