Dimethylformamide → (R)-2-chloro-2-oxo-1-phenylethyl pivalate

Participants

Reaction Conditions

Reaction Steps

(R)-Mandelic acid (10 g, 65.7 mmol) was dissolved in toluene (20 mL) at which point pivaloyl chloride (10.2 mL, 82.9 mmol) was added. This mixture was stirred at 60° C. for 3 hours. After cooling the reaction mixture to 30° C., toluene (10 mL), N,N-dimethylformamide (0.3 mL) and thionyl chloride (10 mL) were added. The reaction mixture was stirred at 35° C. for 2 hours and then at 50° C. for 4 hours. Then the mixture was evaporated to dryness to furnish 14.5 g (R)-2-chloro-2-oxo-1-phenylethyl pivalate as a yellow oil.

Provenance & Evidence