Formaldehyde → Methyl 2-(4-chloro-phenyl)-3-hydroxy-2-methyl-propionate

Participants

Reaction Steps

35 ml of a 1.6 molaric solution of n-butyl lithium (61 mmol) in hexane were dropped to a solution of 8.1 ml (85 mmol) of diisopropylamine in 20 ml of tetrahydrofurane at −78° C. Subsequently, a solution of 10.0 g (50 mmol) of methyl 2-(4-chloro-phenyl)-propionate in 30 ml of tetrahydrofurane were dropped into the reaction mixture at −78° C. and subsequenty formaldehyde was introduced as gas at −20° C. within 30 minutes. The reaction mixture was extracted with ethyl acetate after addition of 5 percent citric acid and glacial acetic acid. The organic phase was washed with IN sulfuric acid, water, saturated sodium bicarbonate solution and sodium chloride solution and died over magnesium sulfate. The raw product was purified over silica gel whereby the eluation was carried out with cyclohexane/ethyl acetate (19:1; 9:1; 4:1; 1:1; and 0:1). The uniform fractions were combined and evaporated down.

Provenance & Evidence