Chloroacetic Acid → 2-Chloroacetophenone

Participants

Reaction Steps

Under the atomosphere of nitrogen gas, diisopropylamine (0.6605 g) was added to 6.67 mL of 0.9 M n-butylmagnesium chloride/tetrahydrofuran (6 mmol). The mixture was stirred a room temperature for 4 hours, after which it was cooled to 0° C. Then, a solution of 284 mg (3.0 mmol) of monochloroacetic acid and 136 mg (1 mmol) of methyl benzoate in 5 mL of tetrahydrofuran was added portionwise for 1 minutes. This mixture was stirred at 0° C. for 30 minutes and, while the temperature was allowed to rise to room temperature, further stirred for 30 minutes. This reaction mixture was poured in 1N-HCl (30 mL) and extracted with ethyl acetate (30 mL×2). The extract was washed with saturated aqueous NaHCO3 solution (30 mL×1) and water (30 mL×1) in that order and dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated to provide a light-yellow oil. Comparative HPLC analysis of this oil with an authentic sample revealed that the oil was predominantly composed of the objective phenacyl chloride (reaction yield 73.7%). Diisopropylbenzamide (reaction yield 0.4%) was obtained as a byproduct.

Provenance & Evidence