2-(4-HYDROXYPHENYL)-2-METHYLPROPANENITRILE

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

Conditions: temp:70.01; pressure:0.00; stir:

Procedure: Dilution of the aliquot (2 uL) with DMSO (200 uL).

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

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Add anhydrous dichloromethane (400 mL) to 2-(4-methoxy-phenyl)-2-methyl-propionitrile (11.93 g, 68.1 mmol) and cool to −78° C. under nitrogen. Then add boron tribromide (33.0 mL, 349 mmol) and stir at −78° C. for 30 minutes. Remove the dry ice/acetone bath and allow the reaction to warm to room temperature. Stir for 3 h and then pour the reaction onto ice. Extract with ethyl acetate (2× 150 mL), dry the extracts over magnesium sulfate, filter, and concentrate on a rotary evaporator to give the crude product. The crude product is purified by flash chromatography on silica gel eluting with 35% ethyl acetate/hexanes to yield 9.79 g (89%) of 2-(4-hydroxy-phenyl)-2-methyl-propionitrile: TLC: Rf in 40% ethyl acetate/hexanes: 0.38; 1H NMR (CDCl3): 7.34-7.32 (m, 2H), 6.86-6.83 (m, 2H), 5.23 (s, 1H), 1.70 (s, 6H). Remove the dry ice/acetone bath the reaction to warm to room temperature pour the reaction onto ice Extract with ethyl acetate (2× 150 mL) dry the extracts over magnesium sulfate filter concentrate on a rotary evaporator to give the crude product The crude product is purified by flash chromatography on silica gel eluting with 35% ethyl acetate/hexanes

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Add anhydrous dichloromethane (400 mL) to 2-(4-methoxy-phenyl)-2-methyl-propionitrile (11.93 g, 68.1 mmol) and cool to −78° C. under nitrogen. Then add boron tribromide (33.0 mL, 349 mmol) and stir at −78° C. for 30 minutes. Remove the dry ice/acetone bath and allow the reaction to warm to room temperature. Stir for 3 h and then pour the reaction onto ice. Extract with ethyl acetate (2×150 mL), dry the extracts over magnesium sulfate, filter, and concentrate on a rotary evaporator to give the crude product. The crude product is purified by flash chromatography on silica gel eluting with 35% ethyl acetate/hexanes to yield 9.79 g (89%) of 2-(4-hydroxy-phenyl)-2-methyl-propionitrile: TLC: Rf in 40% ethyl acetate/hexanes: 0.38; 1H NMR (CDCl3): 7.34-7.32 (m, 2H), 6.86-6.83 (m, 2H), 5.23 (s, 1H), 1.70 (s, 6H). Remove the dry ice/acetone bath the reaction to warm to room temperature pour the reaction onto ice Extract with ethyl acetate (2×150 mL) dry the extracts over magnesium sulfate filter concentrate on a rotary evaporator to give the crude product The crude product is purified by flash chromatography on silica gel eluting with 35% ethyl acetate/hexanes

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Add anhydrous dichloromethane (400 mL) to 2-(4-methoxy-phenyl)-2-methyl-propionitrile (11.93 g, 68.1 mmol) and cool to −78° C. under nitrogen. Then add boron tribromide (33.0 mL, 349 mmol) and stir at −78° C. for 30 minutes. Remove the dry ice/acetone bath and allow the reaction to warm to room temperature. Stir for 3 h and then pour the reaction onto ice. Extract with ethyl acetate (2×150 mL), dry the extracts over magnesium sulfate, filter, and concentrate on a rotary evaporator to give the crude product. The crude product is purified by flash chromatography on silica gel eluting with 35% ethyl acetate/hexanes to yield 9.79 g (89%) of 2-(4-hydroxy-phenyl)-2-methyl-propionitrile: TLC: Rf in 40% ethyl acetate/hexanes: 0.38; 1H NMR (CDCl3): 7.34-7.32 (m, 2H), 6.86-6.83 (m, 2H), 5.23 (s, 1H), 1.70 (s, 6H). Remove the dry ice/acetone bath the reaction to warm to room temperature pour the reaction onto ice Extract with ethyl acetate (2×150 mL) dry the extracts over magnesium sulfate filter concentrate on a rotary evaporator to give the crude product The crude product is purified by flash chromatography on silica gel eluting with 35% ethyl acetate/hexanes

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Add anhydrous dichloromethane (400 mL) to 2-(4-methoxy-phenyl)-2-methyl-propionitrile (11.93 g, 68.1 mmol) and cool to −78° C. under nitrogen. Then add boron tribromide (33.0 mL, 349 mmol) and stir at −78° C. for 30 minutes. Remove the dry ice/acetone bath and allow the reaction to warm to room temperature. Stir for 3 h and then pour the reaction onto ice. Extract with ethyl acetate (2×150 mL), dry the extracts over magnesium sulfate, filter, and concentrate on a rotary evaporator to give the crude product. The crude product is purified by flash chromatography on silica gel eluting with 35% ethyl acetate/hexanes to yield 9.79 g (89%) of 2-(4-hydroxy-phenyl)-2-methyl-propionitrile: TLC: Rf in 40% ethyl acetate/hexanes: 0.38; 1H NMR (CDCl3): 7.34-7.32 (m, 2H), 6.86-6.83 (m, 2H), 5.23 (s, 1H), 1.70 (s, 6H). Remove the dry ice/acetone bath the reaction to warm to room temperature pour the reaction onto ice Extract with ethyl acetate (2×150 mL) dry the extracts over magnesium sulfate filter concentrate on a rotary evaporator to give the crude product The crude product is purified by flash chromatography on silica gel eluting with 35% ethyl acetate/hexanes

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

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Add anhydrous dichloromethane (400 mL) to 2-(4-methoxy-phenyl)-2-methyl-propionitrile (11.93 g, 68.1 mmol) and cool to −78° C. under nitrogen. Then add boron tribromide (33.0 mL, 349 mmol) and stir at −78° C. for 30 minutes. Remove the dry ice/acetone bath and allow the reaction to warm to room temperature. Stir for 3 h and then pour the reaction onto ice. Extract with ethyl acetate (2×150 mL), dry the extracts over magnesium sulfate, filter, and concentrate on a rotary evaporator to give the crude product. The crude product is purified by flash chromatography on silica gel eluting with 35% ethyl acetate/hexanes to yield 9.79 g (89%) of 2-(4-hydroxy-phenyl)-2-methyl-propionitrile: TLC: Rf in 40% ethyl acetate/hexanes: 0.38; 1H NMR (CDCl3): 7.34-7.32 (m, 2H), 6.86-6.83 (m, 2H), 5.23 (s, 1H), 1.70 (s, 6H). Remove the dry ice/acetone bath the reaction to warm to room temperature pour the reaction onto ice Extract with ethyl acetate (2×150 mL) dry the extracts over magnesium sulfate filter concentrate on a rotary evaporator to give the crude product The crude product is purified by flash chromatography on silica gel eluting with 35% ethyl acetate/hexanes

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

Conditions: temp:185.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A process wherein a solventless mixture of Bisphenol A and cyanide ion in the form of sodium cyanide is heated in a closed vessel to about 185° C. and maintained at that temperature for about 20 hours to produce 4-(1-cyano-1-methylethyl)phenol with a conversion of about 100 percent and a selectivity of about 80 percent based on Bisphenol A. maintained at that temperature for about 20 hours

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

Procedure: A preferred manner of practicing this invention constitutes heating a solventless mixture of Bisphenol A and cyanide ion in a closed vessel to about 185° C. and maintaining that temperature for about 20 hours to produce 4-(1-cyano-1-methylethyl)phenol. Preferred conversions and yields based on Bisphenol A are about 100 percent and 80 percent respectively. constitutes heating maintaining that temperature for about 20 hours