反应详情

A solution of ethyl 3-(4-cyano-2-methylphenyl)oxirane-2-carboxylate (927 mg, 4.0 mmol) in 10 mL of dry ethanol was cooled to 0° C. Freshly prepared EtONa (12.4 mmol) in 8 mL of ethanol was added and stirred at 0 for 10 min. Then dropwise addition of 0.1 g of water, stirred at 0° C. for 2 hours, and the sodium salt of the epoxy compound was filtered. The sodium salt of the epoxy compound was then dissolved in 5 mL of water and added 5 mL of 1 N of HCl and 20 mL of toluene. The mixture was heated to reflux for 2 hours. The organic phase was separated, washed by saturated sodium chloride, dried over Na2SO4 and distilled off solvent to afford 130 mg of crude 3-methyl-4-(2-oxoethyl)benzonitrile. MS m/z: 160 (M+1)+.

1. stirringstirred at 0° C. for 2 hours
2. filtrationthe sodium salt of the epoxy compound was filtered
3. dissolutionThe sodium salt of the epoxy compound was then dissolved in 5 mL of water
4. additionadded 5 mL of 1 N of HCl and 20 mL of toluene
5. temperatureThe mixture was heated
6. temperatureto reflux for 2 hours
7. customThe organic phase was separated
8. washwashed by saturated sodium chloride
9. dry with materialdried over Na2SO4
10. distillationdistilled off solvent