Hydrochloric Acid → (R)-3-mesyloxy-2-hydroxy-1-chloropropane

Participants

Reaction Steps

Concentrated HCl (75 ml) was added to (S)-3-mesyloxy-1,2-epoxypropane (6.8 g, 0.045 m). After stirring for 30 minutes, the water was removed through the addition and subsequent evaporation of ethanol. Finally, the residual ethanol was removed at room temperature and 0.1 mm to give (R)-3-mesyloxy-2-hydroxy-1-chloropropane (7.8 g, 92%). This material was dissolved in ether (50 ml) and methanol (10 ml) in an ice bath and sodium (0.94 g, 0.041 m) was added. After stirring for one hour, the mixture was filtered and concentrated at 30°/25 mm. Added acetone, filtered and reconcentrated at 30°/25 mm. Attempted distillation of the residue led to total decomposition; none of the desired (R)-epichlorohydrin was obtained.

Provenance & Evidence