1-Bromodecane → Methyl 8-hydroxyoctadecanoate

Participants

Reaction Conditions

Reaction Steps

Magnesium metal (0.209 g, 8.71 mmol) was added into dry THF (10 ml) in a 50 ml two-necked round bottom flask fitted with a condenser and nitrogen gas inlet. The flask was heated to 70° C., then a few drops of 1,2 dibromoethane were added to the mixture, followed by the slow addition of 1-bromodecane (1.3 g, 5.81 mmol) while at reflux temperature. Stirring was continued for 30 min. After cooling, the Grignard reagent was added dropwise to a stirred solution of methyl 8-oxooctanoate (1.0 g, 5.8 mmol) in THF (10 ml) at −20° C., and the reaction mixture was slowly warmed to room temperature, where stirring was continued for 2 h. The mixture was quenched with saturated ammonium chloride solution, extracted with (3×25 ml) of ethyl acetate, and the combined organic layers were washed with brine solution, dried on anhydrous MgSO4, concentrated and purified on silica gel (2:8 ethyl acetate and hexanes) to obtain an off-white solid (450 mg, 47%).

Provenance & Evidence