3-methyl-2-(2-methylphenyl)butanenitrile

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: To a boiling solution of 2-(2-methylphenyl)-3-methylbutyronitrile (Herz W., J.Am.Chem.Soc. 80, 3139, 1958) (207.9 g) and 86% 3,3-diethoxypropylchloride (154 g) in anhydrous toluene (1250 ml) is dropped during about 50 minutes under stirring 107.7 g of a 50% toluenic sodium amide suspension (NaNH2 content 53.8 g) and the mixture is refluxed under continuous stirring for 6 hours. On subsequent cooling, the stirred mixture is diluted with water (300 ml), the toluenic portion is separated and the aqueous phase is extracted with toluene. The organic solutions are combined, washed with water and saturated brine (aqueous sodium chloride solution) until the reaction is neutral, and then it is dried over anhydrous sodium sulfate. Finally, the solvent is evaporated under reduced pressure and the residue is distilled to give 302.9 g (83.2%) of 5,5-diethoxy-2-isopropyl-2-(2-methylphenyl-valeronitrile, b.p. 102° to 104° C. at 4 Pa. the mixture is refluxed the toluenic portion is separated the aqueous phase is extracted with toluene washed with water and saturated brine (aqueous sodium chloride solution) until the reaction it is dried over anhydrous sodium sulfate Finally, the solvent is evaporated under reduced pressure the residue is distilled

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

Procedure: The alkylation of 2-(2-methylphenyl)-3-methylbutyronitrile of Formula II: ##STR3## with 3,3-diethoxypropylchloride is carried out conveniently in an inert organic solvent in the presence of an alkaline condensing agent. Suitable inert organic solvents are aromatic hydrocarbons, e.g. benzene, toluene or commercial xylene, tertiary amides, e.g. dimethylformamide, or higher-boiling aliphatic ethers, e.g. ethyleneglycol dimethylether. Preferable alkaline condensing agent is sodium hydride or sodium amide. The reaction is advantageously effected by dropping a toluenic sodium amide suspension to a boiling solution of the above reactants in anhydrous toluene and refluxing the mixture for a period of 4 to 10 hours. The so formed acetal, 5,5-diethoxy-2-isopropyl-2-(2-methylphenyl) valeronitrile of Formula III: ##STR4## is isolated on cooling the mixture by short agitation with water, separation of the toluenic phase and evaporation of the solvent. The obtained crude product is purified by distillation under reduced pressure. Preferable alkaline condensing agent refluxing the mixture for a period of 4 to 10 hours

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

Procedure: To a boiling solution of 2-(2-methylphenyl)-3-methylbutyronitrile (Herz W., J.Am.Chem.Soc. 80, 3139, 1958) (207.9 g) and 86% 3,3-diethoxypropylchloride (154 g) in anhydrous toluene (1250 ml) is dropped during about 50 minutes under stirring 107.7 g of a 50% toluenic sodium amide suspension (NaNH2 content 53.8 g) and the mixture is refluxed under continuous stirring for 6 hours. On subsequent cooling, the stirred mixture is diluted with water (300 ml), the toluenic portion is separated and the aqueous phase is extracted with toluene. The organic solutions are combined, washed with water and saturated brine (aqueous sodium chloride solution) until the reaction is neutral, and then it is dried over anhydrous sodium sulfate. Finally, the solvent is evaporated under reduced pressure and the residue is distilled to give 302.9 g (83.2%) of 5,5-diethoxy-2-isopropyl-2-(2-methylphenyl-valeronitrile, b.p. 102° to 104° C. at 4 Pa. the mixture is refluxed the toluenic portion is separated the aqueous phase is extracted with toluene washed with water and saturated brine (aqueous sodium chloride solution) until the reaction it is dried over anhydrous sodium sulfate Finally, the solvent is evaporated under reduced pressure the residue is distilled

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

Procedure: The alkylation of 2-(2-methylphenyl)-3-methylbutyronitrile of Formula II: ##STR3## with 3,3-diethoxypropylchloride is carried out conveniently in an inert organic solvent in the presence of an alkaline condensing agent. Suitable inert organic solvents are aromatic hydrocarbons, e.g. benzene, toluene or commercial xylene, tertiary amides, e.g. dimethylformamide, or higher-boiling aliphatic ethers, e.g. ethyleneglycol dimethylether. Preferable alkaline condensing agent is sodium hydride or sodium amide. The reaction is advantageously effected by dropping a toluenic sodium amide suspension to a boiling solution of the above reactants in anhydrous toluene and refluxing the mixture for a period of 4 to 10 hours. The so formed acetal, 5,5-diethoxy-2-isopropyl-2-(2-methylphenyl) valeronitrile of Formula III: ##STR4## is isolated on cooling the mixture by short agitation with water, separation of the toluenic phase and evaporation of the solvent. The obtained crude product is purified by distillation under reduced pressure. Preferable alkaline condensing agent refluxing the mixture for a period of 4 to 10 hours

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

Procedure: To a solution of 362 g of sodium hydroxide in 362 ml of demineralized water 216.6 g of α-isopropyl-2-methylbenzyl cyanide and 6.4 g of tetrabutylammonium hydrogen sulfate were added, and the mixture was heated to 40° C. with intensive stirring. During 3hours 287 g of allylchloride was added. During, the addition and for further two hours the temperature of the reaction mixture was maintained at 40° C. and thereafter at 60° C. for additional three hours. After cooling to room temperature, the reaction mixture was diluted with 550 ml of water and the product was extracted into toluene. After washing with water until neutral pH and drying with anhydrous magnesium sulfate, the solvent was evaporated and the residue was distilled under diminished pressure to obtain 249 g (93%) of the desired compound, b.p. 122°-124 ° C./333 Pa. During, the addition for further two hours the temperature of the reaction mixture was maintained at 40° C. After cooling to room temperature the product was extracted into toluene After washing with water until neutral pH drying with anhydrous magnesium sulfate the solvent was evaporated the residue was distilled under diminished pressure

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

Procedure: To a solution of 362 g of sodium hydroxide in 362 ml of demineralized water 216.6 g of α-isopropyl-2-methylbenzyl cyanide and 6.4 g of tetrabutylammonium hydrogen sulfate were added, and the mixture was heated to 40° C. with intensive stirring. During 3hours 287 g of allylchloride was added. During, the addition and for further two hours the temperature of the reaction mixture was maintained at 40° C. and thereafter at 60° C. for additional three hours. After cooling to room temperature, the reaction mixture was diluted with 550 ml of water and the product was extracted into toluene. After washing with water until neutral pH and drying with anhydrous magnesium sulfate, the solvent was evaporated and the residue was distilled under diminished pressure to obtain 249 g (93%) of the desired compound, b.p. 122°-124 ° C./333 Pa. During, the addition for further two hours the temperature of the reaction mixture was maintained at 40° C. After cooling to room temperature the product was extracted into toluene After washing with water until neutral pH drying with anhydrous magnesium sulfate the solvent was evaporated the residue was distilled under diminished pressure

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

Procedure: To a boiling solution of 2-(2-methylphenyl)-3-methylbutyronitrile (Herz W., J.Am.Chem.Soc. 80, 3139, 1958) (207.9 g) and 86% 3,3-diethoxypropylchloride (154 g) in anhydrous toluene (1250 ml) is dropped during about 50 minutes under stirring 107.7 g of a 50% toluenic sodium amide suspension (NaNH2 content 53.8 g) and the mixture is refluxed under continuous stirring for 6 hours. On subsequent cooling, the stirred mixture is diluted with water (300 ml), the toluenic portion is separated and the aqueous phase is extracted with toluene. The organic solutions are combined, washed with water and saturated brine (aqueous sodium chloride solution) until the reaction is neutral, and then it is dried over anhydrous sodium sulfate. Finally, the solvent is evaporated under reduced pressure and the residue is distilled to give 302.9 g (83.2%) of 5,5-diethoxy-2-isopropyl-2-(2-methylphenyl-valeronitrile, b.p. 102° to 104° C. at 4 Pa. the mixture is refluxed the toluenic portion is separated the aqueous phase is extracted with toluene washed with water and saturated brine (aqueous sodium chloride solution) until the reaction it is dried over anhydrous sodium sulfate Finally, the solvent is evaporated under reduced pressure the residue is distilled

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

Procedure: The alkylation of 2-(2-methylphenyl)-3-methylbutyronitrile of Formula II: ##STR3## with 3,3-diethoxypropylchloride is carried out conveniently in an inert organic solvent in the presence of an alkaline condensing agent. Suitable inert organic solvents are aromatic hydrocarbons, e.g. benzene, toluene or commercial xylene, tertiary amides, e.g. dimethylformamide, or higher-boiling aliphatic ethers, e.g. ethyleneglycol dimethylether. Preferable alkaline condensing agent is sodium hydride or sodium amide. The reaction is advantageously effected by dropping a toluenic sodium amide suspension to a boiling solution of the above reactants in anhydrous toluene and refluxing the mixture for a period of 4 to 10 hours. The so formed acetal, 5,5-diethoxy-2-isopropyl-2-(2-methylphenyl) valeronitrile of Formula III: ##STR4## is isolated on cooling the mixture by short agitation with water, separation of the toluenic phase and evaporation of the solvent. The obtained crude product is purified by distillation under reduced pressure. Preferable alkaline condensing agent refluxing the mixture for a period of 4 to 10 hours

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

Procedure: To a solution of 362 g of sodium hydroxide in 362 ml of demineralized water 216.6 g of α-isopropyl-2-methylbenzyl cyanide and 6.4 g of tetrabutylammonium hydrogen sulfate were added, and the mixture was heated to 40° C. with intensive stirring. During 3hours 287 g of allylchloride was added. During, the addition and for further two hours the temperature of the reaction mixture was maintained at 40° C. and thereafter at 60° C. for additional three hours. After cooling to room temperature, the reaction mixture was diluted with 550 ml of water and the product was extracted into toluene. After washing with water until neutral pH and drying with anhydrous magnesium sulfate, the solvent was evaporated and the residue was distilled under diminished pressure to obtain 249 g (93%) of the desired compound, b.p. 122°-124 ° C./333 Pa. During, the addition for further two hours the temperature of the reaction mixture was maintained at 40° C. After cooling to room temperature the product was extracted into toluene After washing with water until neutral pH drying with anhydrous magnesium sulfate the solvent was evaporated the residue was distilled under diminished pressure