Methanol → Epibromohydrin

Participants

Reaction Conditions

Reaction Steps

Into a 500-ml flask are placed 36 g of bis(allyl carbonate (0.25 mole) and 100 ml of methanol. This mixture is stirred and cooled in an ice water bath while 80 g of bromine (0.5 mole) is added dropwise. When this reaction is complete, 11 ml of water is added and the mixture stirred while 44 g of a 50 percent aqueous solution of sodium hydroxide (0.55 mole) is added at such a rate so as to maintain reaction temperatures below 55° C. The mixture is then heated to 60° C. for 4 hours and allowed to cool. To this mixture is added 250 ml of water and the resulting water phase is extracted twice with 150-ml portions of methylene chloride. The products are combined and dried over sodium sulfate, filtered and distilled to give a 100 percent conversion of carbonate and 54 percent yield of epibromohydrin. No detectable dibromopropene appeared to be formed.

Provenance & Evidence