2-hydroxy-1-phenylpropan-1-one

反応条件: temp:0.00; pressure:0.00; stir:

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 mixture of 2-hydroxypropiophenone (3.00 g, 20.0 mmol), iodomethane (3.40 g, 24.0 mmol), and K2CO3 (granular, anh.; 13.8 g, 99.9 mmol) was refluxed in acetone (75 mL) for 18 h. The reaction mixture was cooled to room temperature and the inorganic salts were removed by filtration. The filtrate was evaporated under vacuum to give an oil which was subsequently dissolved in diethyl ether (200 mL) and then washed with 0.1N NaOH (3×50 mL) followed by H2O (50 mL). The organic layer was dried (anh. Na2SO4), filtered, and evaporated to an orange oil (3.17 g, 96.9%). This material was used in the following step without further purification. TLC, Rf 0.55 (1% MeOH:1% IPA:CHCl3); GC, tr 4.58 min; MS, m/z 164 (M+1). the inorganic salts were removed by filtration The filtrate was evaporated under vacuum to give an oil which washed with 0.1N NaOH (3×50 mL) The organic layer was dried (anh. Na2SO4) filtered evaporated to an orange oil (3.17 g, 96.9%) This material was used in the following step without further purification tr 4.58 min

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

実験手順: A mixture of 2-hydroxypropiophenone (3.00 g, 20.0 mmol), iodomethane (3.40 g, 24.0 mmol), and K2CO3 (granular, anh.; 13.8 g, 99.9 mmol) was refluxed in acetone (75 mL) for 18 h. The reaction mixture was cooled to room temperature and the inorganic salts were removed by filtration. The filtrate was evaporated under vacuum to give an oil which was subsequently dissolved in diethyl ether (200 mL) and then washed with 0.1N NaOH (3×50 mL) followed by H2O (50 mL). The organic layer was dried (anh. Na2SO4), filtered, and evaporated to an orange oil (3.17 g, 96.9%). This material was used in the following step without further purification. TLC, Rf 0.55 (1% MeOH:1% IPA:CHCl3); GC, tr 4.58 min; MS, m/z 164 (M+1). the inorganic salts were removed by filtration The filtrate was evaporated under vacuum to give an oil which washed with 0.1N NaOH (3×50 mL) The organic layer was dried (anh. Na2SO4) filtered evaporated to an orange oil (3.17 g, 96.9%) This material was used in the following step without further purification tr 4.58 min

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: There was added 10.08 parts of sodium bicarbonate and about 60 parts of water to a mixture of 21.3 parts of α-bromopropiophenone, 6.8 parts of sodium formate and about 90 parts of acetonitrile. The resulting mixture was stirred vigorously for 48 hours at 65° C. during which time carbon dioxide evolved. After cooling, the acetonitrile solution was separated from the aqueous layer and evaporated to dryness. The residue was dissolved into chloroform which was extracted once with water, dried over sodium sulfate, and evaporated to produce analytically pure (>98%) α-hydroxypropiophenone. The yield of this isolated product was 77.1%. After cooling the acetonitrile solution was separated from the aqueous layer evaporated to dryness The residue was dissolved into chloroform which was extracted once with water dried over sodium sulfate evaporated

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

実験手順: 21.5 g of 2-hydroxypropiophenone and 20.6 g of picolinic acid hydrazide are stirred in 250 ml of ethyl cellosolve for 18 hours at 110° C. and then for 2 hours at room temperature. The light yellow solution is concentrated on a rotary evaporator to approx. 50% of its volume. The yellow crystals which have precipitated are isolated by filtration and washed with isopropanol and then with water. After the crystals have been dried under vacuum at 50° C., 18 g of 2-hydroxypropiophenone picolinoylhydrazone are obtained which gives the following microanalysis: The light yellow solution is concentrated on a rotary evaporator to approx. 50% of its volume The yellow crystals which have precipitated are isolated by filtration washed with isopropanol After the crystals have been dried under vacuum at 50° C.

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

実験手順: A mixture of 15.0 g of 2-hydroxypropiophenone and 13.7 g of nicotinic acid hydrazide is stirred in 100 ml of ethyl cellosolve, initially for 18 hours at 120° C. (with distillation of a small amount of solvent) and then for a further 5 hours at room temperature. The light yellow precipitate produced is isolated by suction filtration and washed with ethanol and then with water. 18.5 g of 2-hydroxypropiophenone nicotinoylhydrazone are obtained after the product has been dried at 40°-50° C. under vacuum. 2.7 g of this product are suspended in 30 ml of dimethylformamide and treated with a solution of 2.8 g of nickel(II) acetate·4H2O in 35 ml of dimethylformamide. The resulting mixture is stirred at 120° C. for 4 hours and the product is then isolated by filtration and subsequently washed with isopropanol and then with water. After the product has been dried under vacuum at 60°-70° C., 2.8 g of a yellow powder of the following formula (or a tautomeric form thereof): ##STR17## as the 1:1 nickel complex are obtained which gives the following microanalysis: with distillation of a small amount of solvent) and then for a further 5 hours at room temperature The light yellow precipitate produced is isolated by suction filtration washed with ethanol

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

実験手順: A mixture of 15.0 g of 2-hydroxypropiophenone and 13.7 g of nicotinic acid hydrazide is stirred in 100 ml of ethyl cellosolve, initially for 18 hours at 120° C. (with distillation of a small amount of solvent) and then for a further 5 hours at room temperature. The light yellow precipitate produced is isolated by suction filtration and washed with ethanol and then with water. 18.5 g of 2-hydroxypropiophenone nicotinoylhydrazone are obtained after the product has been dried at 40°-50° C. under vacuum. 2.7 g of this product are suspended in 30 ml of dimethylformamide and treated with a solution of 2.8 g of nickel(II) acetate·4H2O in 35 ml of dimethylformamide. The resulting mixture is stirred at 120° C. for 4 hours and the product is then isolated by filtration and subsequently washed with isopropanol and then with water. After the product has been dried under vacuum at 60°-70° C., 2.8 g of a yellow powder of the following formula (or a tautomeric form thereof): ##STR17## as the 1:1 nickel complex are obtained which gives the following microanalysis: with distillation of a small amount of solvent) and then for a further 5 hours at room temperature The light yellow precipitate produced is isolated by suction filtration washed with ethanol

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

実験手順: There was added 10.08 parts of sodium bicarbonate and about 60 parts of water to a mixture of 21.3 parts of α-bromopropiophenone, 6.8 parts of sodium formate and about 90 parts of acetonitrile. The resulting mixture was stirred vigorously for 48 hours at 65° C. during which time carbon dioxide evolved. After cooling, the acetonitrile solution was separated from the aqueous layer and evaporated to dryness. The residue was dissolved into chloroform which was extracted once with water, dried over sodium sulfate, and evaporated to produce analytically pure (>98%) α-hydroxypropiophenone. The yield of this isolated product was 77.1%. After cooling the acetonitrile solution was separated from the aqueous layer evaporated to dryness The residue was dissolved into chloroform which was extracted once with water dried over sodium sulfate evaporated

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

実験手順: There was added 10.08 parts of sodium bicarbonate and about 60 parts of water to a mixture of 21.3 parts of α-bromopropiophenone, 6.8 parts of sodium formate and about 90 parts of acetonitrile. The resulting mixture was stirred vigorously for 48 hours at 65° C. during which time carbon dioxide evolved. After cooling, the acetonitrile solution was separated from the aqueous layer and evaporated to dryness. The residue was dissolved into chloroform which was extracted once with water, dried over sodium sulfate, and evaporated to produce analytically pure (>98%) α-hydroxypropiophenone. The yield of this isolated product was 77.1%. After cooling the acetonitrile solution was separated from the aqueous layer evaporated to dryness The residue was dissolved into chloroform which was extracted once with water dried over sodium sulfate evaporated

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

実験手順: A mixture of 2-hydroxypropiophenone (3.00 g, 20.0 mmol), iodomethane (3.40 g, 24.0 mmol), and K2CO3 (granular, anh.; 13.8 g, 99.9 mmol) was refluxed in acetone (75 mL) for 18 h. The reaction mixture was cooled to room temperature and the inorganic salts were removed by filtration. The filtrate was evaporated under vacuum to give an oil which was subsequently dissolved in diethyl ether (200 mL) and then washed with 0.1N NaOH (3×50 mL) followed by H2O (50 mL). The organic layer was dried (anh. Na2SO4), filtered, and evaporated to an orange oil (3.17 g, 96.9%). This material was used in the following step without further purification. TLC, Rf 0.55 (1% MeOH:1% IPA:CHCl3) GC, tr 4.58 min; MS, m/z 164 (M+1). the inorganic salts were removed by filtration The filtrate was evaporated under vacuum to give an oil which washed with 0.1N NaOH (3×50 mL) The organic layer was dried (anh. Na2SO4) filtered evaporated to an orange oil (3.17 g, 96.9%) This material was used in the following step without further purification TLC, Rf 0.55 (1% MeOH:1% IPA:CHCl3) GC, tr 4.58 min