反应详情

温度

50 °C

Diethyl(α,α-dimethylbenzyl)malonate was prepared by the conjugate addition of phenyl magnesium bromide to diethyl isopropylidenemalonate as described by C. Holmberg [Liebigs Ann. Chem. 748 (1981)]. A solution of this diester (42.1 g, 0.15 mmol) in ethanol (100 ml) was treated by dropwise addition with a solution of potassium hydroxide (8.48 g, 0.13 mmol) in 100 ml of ethanol. After heating at 90° C. for 1 h and at 50° C. for 20 h, the reaction mixture was evaporated on the rotary evaporator to a residue. The residue was diluted with water and extracted with ether to remove unreacted starting material. The aqueous phase was cooled to 5° C., acidified to pH 3 with 6N HCl, and extracted with methylene chloride. The organic layer was washed with brine solution and dried over magnesium sulfate. Evaporation of the solvent gave 27.3 g (84%) of liquid product. 1H NMR (CDCl3): δ1.05 (t,3H), 1.6 (s,6H), 3.78 (s,1H), 3.96 (m,2H), 7.2-7.4 (m,5H).

1. customthe reaction mixture was evaporated on the rotary evaporator to a residue
2. additionThe residue was diluted with water
3. extractionextracted with ether
4. customto remove unreacted
5. temperatureThe aqueous phase was cooled to 5° C.
6. extractionextracted with methylene chloride
7. washThe organic layer was washed with brine solution
8. dry with materialdried over magnesium sulfate
9. customEvaporation of the solvent