反应详情

6-Bromo-4-phenyl-3,4-dihydro-coumarine (290 g, 0.96 mole) was dissolved in a mixture of methanol (1 L) and acetone (1 L). To the above solution were added potassium carbonate (160 g, 1.16 mole), α-chlorotoluene (140 g, 1.1 mole) and sodium iodide (30 g, 0.47 mole), and the mixture was stirred under reflux for 3 h. The solution was concentrated by distillation, and the residue treated with water and extracted with diethyl ether. The ethereal layer was washed with water, saturated sodium carbonate solution and water, successively. The organic layer was dried over sodium sulfate, filtered and then evaporated to give 420 g (≈100%) of the title compound as a light yellow oil.

1. temperatureunder reflux for 3 h
2. concentrationThe solution was concentrated by distillation
3. additionthe residue treated with water
4. extractionextracted with diethyl ether
5. washThe ethereal layer was washed with water, saturated sodium carbonate solution and water
6. dry with materialThe organic layer was dried over sodium sulfate
7. filtrationfiltered
8. customevaporated