Water → alpha-Trichloromethyl-2-thiophenemethanol

Participants

Reaction Conditions

Reaction Steps

Under a dry argon atmosphere a Grignard reagent was prepared by combining 13.1 g (0.54 mole) of magnesium turnings with 86.4 g (0.53 mole) of 2-bromothiophene in dry diethyl ether. The Grignard reagent was stirred and cooled to 5° C., and 77.8 g (0.53 mole) of chloral was added slowly. The reaction mixture was allowed to stir overnight at room temperature. The reaction mixture was poured into 500 ml of cold water and extracted with three 250 ml portions of ethyl acetate. The combined organic extracts were dried with magnesium sulfate and filtered. The solvent was removed from the filtrate under reduced pressure to yield a liquid. The liquid was distilled under reduced pressure to give 67.2 g of 2,2,2-trichloro-1-(2-thienyl)ethanol; bp 113°-115° C./19.95 pa. The ir spectrum was consistent with the proposed structure.

Provenance & Evidence