Hydrochloric Acid → HCID 68861022, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 80 g (0.333 mol) of methyl3,3-diphenylpropanoate, 42.6 g (0.399 mol) of isobutyryl chloride, and 600 mol of 1,2-dichlorobenzene is cooled to 4° C. Aluminum chloride (112 g, 0.832 mol) is added portion wise over 2 hours while the reaction temperature is kept between −5 and 5° C. The reaction is kept within this temperature range for 7 hours, and then stirred at room temperature for 13 hours. The reaction mixture is poured into a mixture of ice and concentrated hydrochloric acid, and then stirred for 1 hour. The organic layer is washed twice with dilute hydrochloric acid, and then concentrated under vacuum to give 115 grams of crude product. Purification by column chromatography on silica gel with 9:1 heptane:ethyl acetate as the eluent gives 69 g (60% yield) of methyl 3-[4-(2-methylpropionyl)phenyl]-3-phenylpropanoate.

Provenance & Evidence