4-amino-3,5-dimethylbenzaldehyde

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 14.6 g. of 4-amino-3,5-dimethyl-α-[(methylsulfonyl)-methyl]-benzyl alcohol in 50 ml. of absolute dimethylsulfoxide was treated with 1.17 g. of sodium amide, stirred for 2 hours at room temperature, diluted with 500 ml. of water and extracted with two 500 ml. portions of ethyl acetate. The ethyl acetate extract was washed with two 200 ml. portions of water and evaporated under vacuum. After recrystallization of the residue from cyclohexane, there was obtained 4-amino-3,5-dimethyl-benzaldehyde having a melting point of 75°-76° C. diluted with 500 ml of water and extracted with two 500 ml The ethyl acetate extract was washed with two 200 ml portions of water and evaporated under vacuum After recrystallization of the residue from cyclohexane

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 14.6 g. of 4-amino-3,5-dimethyl-α-[(methylsulfonyl)-methyl]-benzyl alcohol in 50 ml. of absolute dimethylsulfoxide was treated with 1.17 g. of sodium amide, stirred for 2 hours at room temperature, diluted with 500 ml. of water and extracted with two 500 ml. portions of ethyl acetate. The ethyl acetate extract was washed with two 200 ml. portions of water and evaporated under vacuum. After recrystallization of the residue from cyclohexane, there was obtained 4-amino-3,5-dimethyl-benzaldehyde having a melting point of 75°-76° C. diluted with 500 ml of water and extracted with two 500 ml The ethyl acetate extract was washed with two 200 ml portions of water and evaporated under vacuum After recrystallization of the residue from cyclohexane

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 14.6 g. of 4-amino-3,5-dimethyl-α-[(methylsulfonyl)-methyl]-benzyl alcohol in 50 ml. of absolute dimethylsulfoxide was treated with 1.17 g. of sodium amide, stirred for 2 hours at room temperature, diluted with 500 ml. of water and extracted with two 500 ml. portions of ethyl acetate. The ethyl acetate extract was washed with two 200 ml. portions of water and evaporated under vacuum. After recrystallization of the residue from cyclohexane, there was obtained 4-amino-3,5-dimethyl-benzaldehyde having a melting point of 75°-76° C. diluted with 500 ml of water and extracted with two 500 ml The ethyl acetate extract was washed with two 200 ml portions of water and evaporated under vacuum After recrystallization of the residue from cyclohexane

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 14.6 g. of 4-amino-3,5-dimethyl-α-[(methylsulfonyl)-methyl]-benzyl alcohol in 50 ml. of absolute dimethylsulfoxide was treated with 1.17 g. of sodium amide, stirred for 2 hours at room temperature, diluted with 500 ml. of water and extracted with two 500 ml. portions of ethyl acetate. The ethyl acetate extract was washed with two 200 ml. portions of water and evaporated under vacuum. After recrystallization of the residue from cyclohexane, there was obtained 4-amino-3,5-dimethyl-benzaldehyde having a melting point of 75°-76° C. diluted with 500 ml of water and extracted with two 500 ml The ethyl acetate extract was washed with two 200 ml portions of water and evaporated under vacuum After recrystallization of the residue from cyclohexane

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 14.6 g. of 4-amino-3,5-dimethyl-α-[(methylsulfonyl)-methyl]-benzyl alcohol in 50 ml. of absolute dimethylsulfoxide was treated with 1.17 g. of sodium amide, stirred for 2 hours at room temperature, diluted with 500 ml. of water and extracted with two 500 ml. portions of ethyl acetate. The ethyl acetate extract was washed with two 200 ml. portions of water and evaporated under vacuum. After recrystallization of the residue from cyclohexane, there was obtained 4-amino-3,5-dimethyl-benzaldehyde having a melting point of 75°-76° C. diluted with 500 ml of water and extracted with two 500 ml The ethyl acetate extract was washed with two 200 ml portions of water and evaporated under vacuum After recrystallization of the residue from cyclohexane

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 2,4,6-trimethylaniline (29.8 g, 0.22 mol) in dioxane (300 mL) DDQ (49.9 g, 0.22 mol) is added. The brown suspension is stirred at rt for 18 h before it is filtered. The solvent of the filtrate is evaporated and the crude product is purified by CC on silica gel eluting with hexane:EA 1:1 to give 4-amino-3,5-dimethyl-benzaldehyde (5.0 g) as a beige solid; LC-MS: tR=0.78 min, [M+1]+=150.26. is filtered The solvent of the filtrate is evaporated the crude product is purified by CC on silica gel eluting with hexane:EA 1:1

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 2,4,6-trimethylaniline (29.8 g, 0.22 mol) in dioxane (300 mL) DDQ (49.9 g, 0.22 mol) is added. The brown suspension is stirred at rt for 18 h before it is filtered. The solvent of the filtrate is evaporated and the crude product is purified by CC on silica gel eluting with hexane:EA 1:1 to give 4-amino-3,5-dimethyl-benzaldehyde (5.0 g) as a beige solid; LC-MS: tR=0.78 min, [M+1]+=150.26. is filtered The solvent of the filtrate is evaporated the crude product is purified by CC on silica gel eluting with hexane:EA 1:1

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 2,4,6-trimethylaniline (29.8 g, 0.22 mol) in dioxane (300 mL) DDQ (49.9 g, 0.22 mol) is added. The brown suspension is stirred at rt for 18 h before it is filtered. The solvent of the filtrate is evaporated and the crude product is purified by CC on silica gel eluting with hexane:EA 1:1 to give 4-amino-3,5-dimethyl-benzaldehyde (5.0 g) as a beige solid; LC-MS: tR=0.78 min, [M+1]+=150.26. is filtered The solvent of the filtrate is evaporated the crude product is purified by CC on silica gel eluting with hexane:EA 1:1

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 14.6 g. of 4-amino-3,5-dimethyl-α-[(methylsulfonyl)-methyl]-benzyl alcohol in 50 ml. of absolute dimethylsulfoxide was treated with 1.17 g. of sodium amide, stirred for 2 hours at room temperature, diluted with 500 ml. of water and extracted with two 500 ml. portions of ethyl acetate. The ethyl acetate extract was washed with two 200 ml. portions of water and evaporated under vacuum. After recrystallization of the residue from cyclohexane, there was obtained 4-amino-3,5-dimethyl-benzaldehyde having a melting point of 75°-76° C. diluted with 500 ml of water and extracted with two 500 ml The ethyl acetate extract was washed with two 200 ml portions of water and evaporated under vacuum After recrystallization of the residue from cyclohexane

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 14.6 g. of 4-amino-3,5-dimethyl-α-[(methylsulfonyl)-methyl]-benzyl alcohol in 50 ml. of absolute dimethylsulfoxide was treated with 1.17 g. of sodium amide, stirred for 2 hours at room temperature, diluted with 500 ml. of water and extracted with two 500 ml. portions of ethyl acetate. The ethyl acetate extract was washed with two 200 ml. portions of water and evaporated under vacuum. After recrystallization of the residue from cyclohexane, there was obtained 4-amino-3,5-dimethyl-benzaldehyde having a melting point of 75°-76° C. diluted with 500 ml of water and extracted with two 500 ml The ethyl acetate extract was washed with two 200 ml portions of water and evaporated under vacuum After recrystallization of the residue from cyclohexane