反应详情

A solution of 15.7 g cyclododecene and 15.8 g dichlorourethane in 125 ml of benzene was refluxed for 12 hours under a nitrogen atmosphere. The reaction mixture was cooled, diluted with 100 ml of ether and then washed repeatedly with saturated sodiumbisulfite solution. After washing with brine the organic layer was dried and concentrated to give 19.5 g of crudechlorourethane. This was heated at 100°-120° C. for 6 hours. The resulting thick dark oil was diluted with hexane and allowed to stand in the freezer overnight. The solid was filtered and recrystallized from hexane/dichloromethane to give 5.66 g of white crystals, m.p. 84°-86° C. The mother liquor was concentrated to give 5.23 g of thick oil which after flash chromatography (silica gel; ethyl acetate/hexane) gave additional 1.23 g of white crystals, m.p. 85° C. and 0.96 g of a clear oil, which slowly solidified. Recrystallization from hexane gave 0.25 g of crystals, m.p. 72°-74° C.

1. temperatureThe reaction mixture was cooled
2. washwashed repeatedly with saturated sodiumbisulfite solution
3. washAfter washing with brine the organic layer
4. customwas dried
5. concentrationconcentrated
6. customto give 19.5 g of crudechlorourethane
7. temperatureThis was heated at 100°-120° C. for 6 hours
8. customto stand in the freezer overnight
9. filtrationThe solid was filtered
10. customrecrystallized from hexane/dichloromethane