反应详情

1-(2-Cyclohexen-1-yl)-2,2,2-trichloroethanol (20 g; 87.3 m. moles) was added to a solution of cupric chloride dihydrate (0.25 g; 1.47 m. moles) and a 1,10-phenanthroline hydrate (0.75 g; 3.8 m. moles) in methanol (150 ml). A rapid stream of oxygen was passed through the vigorously stirred solution and a solution of sodium (2.5 g; 108.5 m. moles) in methanol (50 ml) was added over a period of 41/4 hours. A solution of cupric chloride dihydrate (0.125 g; 0.733 m. moles) and 1,10-phenanthroline hydrate (0.375 g; 1.9 m. moles) in methanol (10 ml) was then added and the reaction allowed to proceed for a further 11/4 hours at a temperature of 20°-25° C. The reaction mixture was poured into ice-cold dilute hydrochloric acid, extracted with ether (4×100 ml) and the combined extracts washed twice with dilute aqueous sodium carbonate. The dried (MgSO4) extract was evaporated and the residue distilled to give a mixture of methyl 2-cyclohexene-1-carboxylate and methyl 1-cyclohexene-1-carboxylate (7.2 g; yield 59%), b.p. 80°-85° C./12 mm, containing about 90% of the former as indicated by G.L.C.

1. custom4 hours
2. customat a temperature of 20°-25° C
3. additionThe reaction mixture was poured into ice-cold dilute hydrochloric acid
4. extractionextracted with ether (4×100 ml)
5. washthe combined extracts washed twice with dilute aqueous sodium carbonate
6. dry with materialThe dried (MgSO4)
7. extractionextract
8. customwas evaporated
9. distillationthe residue distilled
10. customto give