Lactic Acid → HCID 54500398, compound

Participants

Reaction Steps

153 ml (1.1 mol) of tert.butyl bromide are slowly added dropwise to a suspension of 10 g (0.11 mol) of L (+)-lactic acid and 94.2 g (1.1 mol) of sodium bicarbonate in 200 ml of dimethyl sulphoxide. The mixture is stirred for 48 hours, then poured into 1 liter of water and extracted twice with 100 ml of ethyl acetate each time. The organic phase is back-washed three times with 200 ml of water each time and subsequently evaporated. The crude product is chromatographed on a 20-fold amount of silica gel with n-hexane/ethyl acetate (4:1) and the eluate is evaporated. There are obtained 5.7 g of L (-)-lactic acid [(methylthio)methyl] ester; [α]D20 =-39.27° (c=1.3% in chloroform).

Provenance & Evidence