Hydrochloric Acid → o-(4'-Nitrobenzoylvinyl)benzoyl chloride

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Reaction Steps

A 500 ml flask fitted with a reflux condenser was charged with 29.7 grams (0.1 mol) of 3-(4-nitrophenacyl)phthalide, 0.12 mol of freshly distilled thionyl chloride and 100 ml of benzene. The mixture was heated to reflux temperature on a steambath, and a clear solution formed on initiation of refluxing, with evolution of HCl. The evolution ceased after 1 hour, after which benzene and excess unreacted thionyl chloride were distilled off under reduced pressure. The residual solid in the flask was triturated with ligroin, filtered and dried to yield o-(4'-nitrobenzoylvinyl)benzoyl chloride, m.p. 133°-134° C. Analysis shows 59.4% carbon, 3.36% hydrogen, 4.56% nitrogen and 11.72% chlorine as against calculated values of 60.87%, 3.19%, 4.44% and 11.23% for C16H10ClNO4.

Provenance & Evidence