反应详情

A mixture of 52 grams (0.31 mol) of 4-isobutylphenylacetonitrile (Preparation 1) and 230 grams (1.95 mols) of diethyl carbonate was heated in a flask provided with a thermometer, stirrer, dropping funnel, and distillation column having a length of 19 centimeters filled with Fenske rings. When the temperature of the mixture had reached 90° C, a solution of sodium ethoxide in ethanol that was freshly prepared from 9.2 grams (0.4 mol) of sodium metal and 200 milliliters of ethanol was added drop by drop from the dropping funnel while the vapors formed were permitted to distill through the distillation column. After the temperature reached between 120° and 130° C, no further vapors were distilled and the mixture was stirred vigorously for an additional period of 1 hour. Thereafter, the mixture remaining in the flask was cooled and the flask was surrounded with cracked ice and a solution of 35 milliliters of glacial acetic acid in 130 milliliters of water was added thereto with stirring. The organic phase was then separated from the aqueous phase. The aqueous phase was extracted with ether and the extract was combined with the organic phase, which was then successively washed with a saturated aqueous solution of sodium bicarbonate and water and dried over anhydrous magnesium sulfate. The dried liquid was then filtered to separate the solids therefrom and the filtrate was distilled under vacuum, the fraction distilling between 150° and 155° C at a pressure of 1 millimeter of mercury, which is the ethyl 2-(4-isobutylphenyl)cyanoacetate, was collected.

1. temperaturewas heated in a flask
2. customprovided with a thermometer, stirrer
3. distillationdistillation column
4. additionfilled with Fenske rings
5. customhad reached 90° C
6. additionwas added drop by drop from the dropping funnel while the vapors
7. customformed
8. distillationto distill through the distillation column
9. customreached between 120° and 130° C
10. distillationno further vapors were distilled
11. temperaturewas cooled
12. additiona solution of 35 milliliters of glacial acetic acid in 130 milliliters of water was added
13. stirringwith stirring
14. customThe organic phase was then separated from the aqueous phase
15. extractionThe aqueous phase was extracted with ether
16. washwas then successively washed with a saturated aqueous solution of sodium bicarbonate and water
17. dry with materialdried over anhydrous magnesium sulfate
18. filtrationThe dried liquid was then filtered
19. customto separate the solids
20. distillationthe filtrate was distilled under vacuum
21. distillationthe fraction distilling between 150° and 155° C at a pressure of 1 millimeter of mercury, which
22. customwas collected