Benzenepropanoyl chloride → 4-Methyl-1-phenylpentan-3-one

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Reaction Steps

Lithium chloride (27 mmol) and copper (I) chloride (13.46 mmol) are weighed into a flame dried 250 mL round-bottomed flask fitted with low temperature thermometer. Dry THF (50 mL) is added and the mixture stirred at RT for 1 h to give a cloudy yellow-green solution. This is cooled to −55° C. and isopropylmagnesium chloride (6.75 mL of a 2 M solution in THF, 13.5 mmol) is added. After 15 min hydrocinnamoyl chloride (13.46 mmol) is added quickly at −60° C. and the mixture allowed to warm slowly to RT overnight. The mixture is quenched with water (100 mL) and 35% ammonium hydroxide (20 mL) is added. The mixture is stirred at RT for 1 h and then extracted with diethyl ether (3×50 mL). The combined ether extracts are washed with saturated brine (50 mL), dried (MgSO4), filtered and evaporated under reduced pressure to give 4-methyl-1-phenyl-pentan-3-one.

Provenance & Evidence