2,6-Dimethylbenzonitrile

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 2,6-dimethylbenzonitrile (5.0 g, 38.0 mmol), bromine (1.9 ml, 38.0 mmol) and chloroform (10 ml) is stirred at room temperature for 24 hours and subsequently heated to 60° C. for 6 hours. Upon cooling down to 0° C., 10 g of AlCl3 are added and the mixture is stirred for 4 hours at 0° C. The reaction mixture is poured into water and extracted with toluene. The organic phase is separated and concentrated and the residue is purified by column chromatography yielding the pure product as brown crystals, 6.2 g, mp. 60° C. subsequently heated to 60° C. for 6 hours Upon cooling down to 0° C. the mixture is stirred for 4 hours at 0° C extracted with toluene The organic phase is separated concentrated the residue is purified by column chromatography

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

Procedure: A mixture of 2,6-dimethylbenzonitrile (5.0 g, 38.0 mmol), bromine (1.9 ml, 38.0 mmol) and chloroform (10 ml) is stirred at room temperature for 24 hours and subsequently heated to 60° C. for 6 hours. Upon cooling down to 0° C., 10 g of AlCl3 are added and the mixture is stirred for 4 hours at 0° C. The reaction mixture is poured into water and extracted with toluene. The organic phase is separated and concentrated and the residue is purified by column chromatography yielding the pure product as brown crystals, 6.2 g, mp. 60° C. subsequently heated to 60° C. for 6 hours Upon cooling down to 0° C. the mixture is stirred for 4 hours at 0° C extracted with toluene The organic phase is separated concentrated the residue is purified by column chromatography

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

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

Procedure: The preparation of 2,6-dimethyl DL-phenylalanines is disclosed by R. R. Herr, T. Enkoji & J. P. Dailey, J. Amer. Chem. Soc., 79, 4229(1957). The method involves the conversion of 2,6-dimethyl aniline into its diazonium salt, followed by treatment with potassium cyanide and cuprous cyanide to produce 2,6-dimethylbenzonitrile. The benzonitrile is reduced with lithium aluminum hydride to provide 2,6-dimethylbenzylamine, which is reacted with excess methyl iodide producing 2,6dimethylbenzyltrimethylammonium iodide. The trimethylammonium group is displaced with diethyl-2acetamidomalonate to form the amido diester, which is subsequently acidolysed to form the racemic mixture of 2,6-dimethylphenylalanine.

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

Procedure: The preparation of 2,6-dimethyl DL-phenylalanines is disclosed by R. R. Herr, T. Enkoji & J. P. Dailey, J. Amer. Chem. Soc., 79, 4229(1957). The method involves the conversion of 2,6-dimethyl aniline into its diazonium salt, followed by treatment with potassium cyanide and cuprous cyanide to produce 2,6-dimethylbenzonitrile. The benzonitrile is reduced with lithium aluminum hydride to provide 2,6-dimethylbenzylamine, which is reacted with excess methyl iodide producing 2,6dimethylbenzyltrimethylammonium iodide. The trimethylammonium group is displaced with diethyl-2acetamidomalonate to form the amido diester, which is subsequently acidolysed to form the racemic mixture of 2,6-dimethylphenylalanine.

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

Procedure: To a stirred solution of 2,6-dimethylbenzonitrile (1 g, 7.6 mmol) in THF (15 mL) under argon at 0° C. a solution of DIBAL (1 M in THF, 8 mL, 8 mmol) was added dropwise over 5 minutes. After 3 hr at 0° C., the reaction mixture was brought to room temperature and stirred overnight. The reaction was quenched with 5% sulfuric acid at 0° C., extracted with ether, washed with brine and dried (MgSO4). Concentration provided 2,6-dimethylbenzaldehyde (0.9 g) which was used without further purification. was brought to room temperature The reaction was quenched with 5% sulfuric acid at 0° C. extracted with ether washed with brine dried (MgSO4) Concentration

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

Procedure: A mixture of 2,6-dimethylbenzonitrile (5.0 g, 38.0 mmol), bromine (1.9 ml, 38.0 mmol) and chloroform (10 ml) is stirred at room temperature for 24 hours and subsequently heated to 60° C. for 6 hours. Upon cooling down to 0° C., 10 g of AlCl3 are added and the mixture is stirred for 4 hours at 0° C. The reaction mixture is poured into water and extracted with toluene. The organic phase is separated and concentrated and the residue is purified by column chromatography yielding the pure product as brown crystals, 6.2 g, mp. 60° C. subsequently heated to 60° C. for 6 hours Upon cooling down to 0° C. the mixture is stirred for 4 hours at 0° C extracted with toluene The organic phase is separated concentrated the residue is purified by column chromatography

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