Tetrahydrofuran → 2,2-Dihydroxy-3'-(alpha,alpha,alpha-trifluoro-m-tolyloxy)acetophenone

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3.10 g of methyl methyl thiomethylsulfoxide in 20 ml of tetrahydrofuran under argon in an ice bath was added 10.4 ml. of 2.4M n-butyllithium in hexane via a syringe during 15 minutes, maintaining the temperature at 10°-15° C. The mixture was stirred at 10° C. for 10 minutes, then recooled and a solution of 5.32 g of m-[m-(trifluoromethyl)phenoxy]benzaldehyde in 10 ml of tetrahydrofuran was added during 10 minutes, maintaining the temperature at <10° C. The resulting solution was stirred at 0°-5° C. for one hour, then the tetrahydrofuran was evaporated. The resulting yellow foam was added to dimethyl sulfoxide and cooled in an ice bath while aqueous hydrobromic acid was added. The reaction was then heated at 50° C. overnight, then poured into ice and extracted with ethyl acetate. The extract was washed with water, saturated sodium bicarbonate and brine, dried and evaporated, giving 2,2-dihydroxy-3'-(α,α,α-trifluoro-m-tolyloxy)acetophenone as a yellow oil.

Provenance & Evidence