Diethyl Sulfate → HCID 66921047, compound

Participants

Reaction Conditions

Reaction Steps

After mixing 259.1 g of potassium carbonate (1.88 mol, granular reagent), 985 mL of tert-butyl methyl ether, 493 mL of N,N-dimethylformamide and 202.4 g (1.31 mol) of diethyl sulfate, a mixture of 328.4 g (1.25 mol) of 2-(2-(4-chlorophenoxy)phenyl)acetic acid and 164 mL of N,N-dimethylformamide was added dropwise to the obtained mixture over a period of one hour. The internal temperature of the mixture during the dropwise addition was 25-40° C. Upon completion of the dropwise addition, the obtained mixture was stirred at 25° C. for 12 hours, and completion of the reaction was confirmed by high-performance liquid chromatography. A 1642 mL portion of water was slowly added dropwise to suspend the reaction. The internal temperature of the mixture during the dropwise addition was 25-35° C. The obtained mixture was subjected to liquid separation, and after washing the organic layer with 656 mL of water and 495 mL of brine in that order, the obtained organic layer was subjected to dehydration treatment with anhydrous magnesium sulfate and the treated organic layer was concentrated to obtain 366.4 g of crude ethyl 2-(2-(4-chlorophenoxy)phenyl)acetate as an oil.

Provenance & Evidence