Methanol → Epibromohydrin

Temperature

60 °C

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.

1. customInto a 500-ml flask are placed
2. additionis added dropwise
3. additionis added at such a rate so as
4. temperatureto maintain
5. customreaction temperatures below 55° C
6. temperatureto cool
7. extractionthe resulting water phase is extracted twice with 150-ml portions of methylene chloride
8. dry with materialdried over sodium sulfate
9. filtrationfiltered
10. distillationdistilled

ORD record

ord-64d73912f9244bc8b03749d3c8d3e22e

Source dataset

uspto-grants-1986_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04568759