2-Ethylphenol → Ethyl 2-(4-(chlorosulfonyl)-2-ethylphenoxy)acetate

Participants

Reaction Steps

A solution of 2-ethylphenol (24.4 g, 200 mmol), potassium carbonate (41.4 g, 300 mmol) and ethyl bromoacetate (36.7 g, 220 mmol) in 2-butanone (250 ml) was stirred at 100° C. for 24 h. The reaction mixture was filtered and evaporated. The residue was dissolved in benzol (100 ml), washed with sodium carbonate solution (5%, 25 ml), dried and evaporated. The residue was dissolved in dichloromethane (100 ml) and chlorosulfonic acid (34.9 g, 300 mmol) was added slowly at −5° C. The reaction mixture was stirred at room temperature for 6 h. Ice water (25 ml) was added and the mixture was extracted with dichloromethane (3×100 ml). The combined organic phases were washed with water, dried and evaporated to give crude (4-chlorosulfonyl-2-ethyl-phenoxy)-acetic acid ethyl ester as an oil. Crystallization from heptane (500 ml) gave the desired product in 31.6 g (52%) yield.

Provenance & Evidence