2-[4-(2-methylpropyl)phenyl]acetonitrile

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1.73 g of 4-isobutylphenylacetonitrile and 10 g of 95% of 2,2,2-trifluoroethanol and 10 g of concentrated sulfuric acid were refluxed for 12 hours. After the reaction was complete, ice-water was added to the mixture. The resulting mixture was extracted with ether. The ether layer separated was dehydrated and concentrated to leave an oily residue. The residue was distilled in vacuo to give 1.4 g of 4-isobutylphenylacetic acid-2,2,2-trifluoroethyl ester as a pale yellow oil, boiling at 77°-79° C./1 mmHg. Analysis-Calculated for C14H17F3O2 : C, 61.30; H, 6.25. Found: C, 61.21; H, 6.23. were refluxed for 12 hours The resulting mixture was extracted with ether The ether layer separated concentrated to leave an oily residue The residue was distilled in vacuo

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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. was heated in a flask provided with a thermometer, stirrer distillation column filled with Fenske rings had reached 90° C was added drop by drop from the dropping funnel while the vapors formed to distill through the distillation column reached between 120° and 130° C no further vapors were distilled was cooled a solution of 35 milliliters of glacial acetic acid in 130 milliliters of water was added with stirring The organic phase was then separated from the aqueous phase The aqueous phase was extracted with ether was then successively washed with a saturated aqueous solution of sodium bicarbonate and water dried over anhydrous magnesium sulfate The dried liquid was then filtered to separate the solids the filtrate was distilled under vacuum the fraction distilling between 150° and 155° C at a pressure of 1 millimeter of mercury, which was collected

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1.73 g of 4-isobutylphenylacetonitrile and 10 g of 95% of 2,2,2-trifluoroethanol and 10 g of concentrated sulfuric acid were refluxed for 12 hours. After the reaction was complete, ice-water was added to the mixture. The resulting mixture was extracted with ether. The ether layer separated was dehydrated and concentrated to leave an oily residue. The residue was distilled in vacuo to give 1.4 g of 4-isobutylphenylacetic acid-2,2,2-trifluoroethyl ester as a pale yellow oil, boiling at 77°-79° C./1 mmHg. Analysis-Calculated for C14H17F3O2 : C, 61.30; H, 6.25. Found: C, 61.21; H, 6.23. were refluxed for 12 hours The resulting mixture was extracted with ether The ether layer separated concentrated to leave an oily residue The residue was distilled in vacuo

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1.73 g of 4-isobutylphenylacetonitrile and 10 g of 95% of 2,2,2-trifluoroethanol and 10 g of concentrated sulfuric acid were refluxed for 12 hours. After the reaction was complete, ice-water was added to the mixture. The resulting mixture was extracted with ether. The ether layer separated was dehydrated and concentrated to leave an oily residue. The residue was distilled in vacuo to give 1.4 g of 4-isobutylphenylacetic acid-2,2,2-trifluoroethyl ester as a pale yellow oil, boiling at 77°-79° C./1 mmHg. Analysis-Calculated for C14H17F3O2 : C, 61.30; H, 6.25. Found: C, 61.21; H, 6.23. were refluxed for 12 hours The resulting mixture was extracted with ether The ether layer separated concentrated to leave an oily residue The residue was distilled in vacuo

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 550 g of ethyl bromide are added drop-wise to 470 g of 4-isobutylphenyl acetonitrile, 1550 g of a 50% solution of sodium hydroxide and 11.4 g of triethylbenzyl ammonium chloride. The addition is complete within 2 hours. During this addition, the temperature must be controlled such that it does not exceed 40° C. The mixture is agitated for 10 hours at 40° C. After cooling of the mixture, the alkaline phase is discarded and the organic layer is washed with water until neutral. Fractionation yields 536 g of crude 2-(4-isobutylphenyl)butyronitrile. The addition During this addition does not exceed 40° C After cooling of the mixture the organic layer is washed with water until neutral

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 527 g of 4-isobutylbenzyl chloride, 153 g of sodium cyanide and 720 ml of dimethylsulfoxide are agitated for 6 hours at 40° C. The mixture is cooled and then diluted with water. An oily layer separates and is extracted with ether. The ether solution is subjected to fractionation and yields 367 g of 4-isobutylphenyl acetonitrile. The mixture is cooled An oily layer separates and is extracted with ether

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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. was heated in a flask provided with a thermometer, stirrer distillation column filled with Fenske rings had reached 90° C was added drop by drop from the dropping funnel while the vapors formed to distill through the distillation column reached between 120° and 130° C no further vapors were distilled was cooled a solution of 35 milliliters of glacial acetic acid in 130 milliliters of water was added with stirring The organic phase was then separated from the aqueous phase The aqueous phase was extracted with ether was then successively washed with a saturated aqueous solution of sodium bicarbonate and water dried over anhydrous magnesium sulfate The dried liquid was then filtered to separate the solids the filtrate was distilled under vacuum the fraction distilling between 150° and 155° C at a pressure of 1 millimeter of mercury, which was collected

Conditions: temp:0.00; pressure:0.00; stir: