2-Methylene-1,3-propanediol

3775-29-9

3513-81-3

General procedure for the synthesis of 2-methylene-1,3-propanediol from 2-methylenepropane-1,3-diyl diacetate: allyl alcohol (1 eq.) was dissolved with acetic anhydride (1.2 eq.) in dichloromethane (DCM, concentration ca. 1 M) at 0 °C. Subsequently, pyridine (1 eq.) and 4-dimethylaminopyridine (DMAP, 0.1 mol%) were added to the reaction system. The reaction mixture was kept stirred at 0 °C for 30 min and then gradually warmed up to room temperature. After completion of the reaction, the reaction was quenched with 2N hydrochloric acid solution, the organic layer was separated, washed sequentially with water and brine and finally dried with anhydrous sodium sulfate. The solvent was removed by careful evaporation under reduced pressure to give pure 2-methylene propane-1,3-diyl diacetate (2d) without further purification. Subsequent processing was carried out via Method B. Specifically, purification by column chromatography (eluent ratio hexane:ethyl acetate = 20:1) afforded 2-methylene-1,3-propanediol as a colorless oil (20 g, 91% yield). The analytical data of the resulting compound were in agreement with literature reports.