2-ethylsulfonylethanol

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

Procedure: To a solution of 6.6 g (0.03 mole) of 1-piperazinecarboxylic acid, phenylmethyl ester in 100 ml of N,N-dimethylformamide was added, in portions, 1.44 g (0.03 mole) of a 50% sodium hydride suspension in mineral oil. The mixture was heated at 50° for 1 hr and allowed to cool slightly. To it was added dropwise a solution of 8.8 g (0.003 mole) of 2-(ethylsulfonyl)ethanol, 4-methylbenzenesulfonate in 30 ml of N,N-dimethylformamide. The mixture was heated at 50° for 1 hr, allowed to cool, concentrated under vacuum to one-half the original volume, allowed to stand for four days and then concentrated to a paste. The paste was diluted with ether and the suspension filtered to remove insoluble salts. The filtrate was concentrated and chromatographed over 250 g of silica gel with 1 l each of the following solutions of methanol in ethyl acetate: 1.5%, 3% and 15%. That portion of the eluent containing the product, Rf(silica--10 % methanol/ethyl acetate)=0.7, was concentrated to dryness under vacuum to afford 8.3 g (81%) of the desired product as an oil. The IR and NMR spectra were consistent with the assigned structure. The mixture was heated at 50° for 1 hr to cool slightly The mixture was heated at 50° for 1 hr to cool concentrated under vacuum to one-half the original volume concentrated to a paste The paste was diluted with ether the suspension filtered to remove insoluble salts The filtrate was concentrated chromatographed over 250 g of silica gel with 1 l each of the following solutions of methanol in ethyl acetate That portion of the eluent containing the product, Rf(silica--10 % methanol/ethyl acetate)=0.7 was concentrated to dryness under vacuum

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

Procedure: To a solution of 6.6 g (0.03 mole) of 1-piperazinecarboxylic acid, phenylmethyl ester in 100 ml of N,N-dimethylformamide was added, in portions, 1.44 g (0.03 mole) of a 50% sodium hydride suspension in mineral oil. The mixture was heated at 50° for 1 hr and allowed to cool slightly. To it was added dropwise a solution of 8.8 g (0.003 mole) of 2-(ethylsulfonyl)ethanol, 4-methylbenzenesulfonate in 30 ml of N,N-dimethylformamide. The mixture was heated at 50° for 1 hr, allowed to cool, concentrated under vacuum to one-half the original volume, allowed to stand for four days and then concentrated to a paste. The paste was diluted with ether and the suspension filtered to remove insoluble salts. The filtrate was concentrated and chromatographed over 250 g of silica gel with 1 l each of the following solutions of methanol in ethyl acetate: 1.5%, 3% and 15%. That portion of the eluent containing the product, Rf(silica--10 % methanol/ethyl acetate)=0.7, was concentrated to dryness under vacuum to afford 8.3 g (81%) of the desired product as an oil. The IR and NMR spectra were consistent with the assigned structure. The mixture was heated at 50° for 1 hr to cool slightly The mixture was heated at 50° for 1 hr to cool concentrated under vacuum to one-half the original volume concentrated to a paste The paste was diluted with ether the suspension filtered to remove insoluble salts The filtrate was concentrated chromatographed over 250 g of silica gel with 1 l each of the following solutions of methanol in ethyl acetate That portion of the eluent containing the product, Rf(silica--10 % methanol/ethyl acetate)=0.7 was concentrated to dryness under vacuum

Conditions: temp:95.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 20.4 g (0.1 mol) of 1,4-dihydroxy-2-naphthoic acid and 19 g (0.1 mol) of p-toluenesulfonic acid were added to 200 ml of dehydrated toluene. To the mixture, 27.6 g (0.2 mol) of β-ethylsulfonylethanol was added dropwise for 30 minutes under heating at 95° C. with stirring. After heating with stirring for 7 hours, the mixture was cooled to 20° to 30° C. 100 ml of acetonitrile was added to the mixture, the solid deposited was separated by filtration to obtain 17.2 g (53%) of 1-hydroxy-4-(β-ethylsulfonylethoxy)-2-naphthoic acid. After heating with stirring for 7 hours the mixture was cooled to 20° to 30° C the solid deposited was separated by filtration

Conditions: temp:95.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 20.4 g (0.1 mol) of 1,4-dihydroxy-2-naphthoic acid and 19 g (0.1 mol) of p-toluenesulfonic acid were added to 200 ml of dehydrated toluene. To the mixture, 27.6 g (0.2 mol) of β-ethylsulfonylethanol was added dropwise for 30 minutes under heating at 95° C. with stirring. After heating with stirring for 7 hours, the mixture was cooled to 20° to 30° C. 100 ml of acetonitrile was added to the mixture, the solid deposited was separated by filtration to obtain 17.2 g (53%) of 1-hydroxy-4-(β-ethylsulfonylethoxy)-2-naphthoic acid. After heating with stirring for 7 hours the mixture was cooled to 20° to 30° C the solid deposited was separated by filtration

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

Procedure: To a solution of 6.6 g (0.03 mole) of 1-piperazinecarboxylic acid, phenylmethyl ester in 100 ml of N,N-dimethylformamide was added, in portions, 1.44 g (0.03 mole) of a 50% sodium hydride suspension in mineral oil. The mixture was heated at 50° for 1 hr and allowed to cool slightly. To it was added dropwise a solution of 8.8 g (0.003 mole) of 2-(ethylsulfonyl)ethanol, 4-methylbenzenesulfonate in 30 ml of N,N-dimethylformamide. The mixture was heated at 50° for 1 hr, allowed to cool, concentrated under vacuum to one-half the original volume, allowed to stand for four days and then concentrated to a paste. The paste was diluted with ether and the suspension filtered to remove insoluble salts. The filtrate was concentrated and chromatographed over 250 g of silica gel with 1 l each of the following solutions of methanol in ethyl acetate: 1.5%, 3% and 15%. That portion of the eluent containing the product, Rf(silica--10 % methanol/ethyl acetate)=0.7, was concentrated to dryness under vacuum to afford 8.3 g (81%) of the desired product as an oil. The IR and NMR spectra were consistent with the assigned structure. The mixture was heated at 50° for 1 hr to cool slightly The mixture was heated at 50° for 1 hr to cool concentrated under vacuum to one-half the original volume concentrated to a paste The paste was diluted with ether the suspension filtered to remove insoluble salts The filtrate was concentrated chromatographed over 250 g of silica gel with 1 l each of the following solutions of methanol in ethyl acetate That portion of the eluent containing the product, Rf(silica--10 % methanol/ethyl acetate)=0.7 was concentrated to dryness under vacuum

Conditions: temp:95.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 20.4 g (0.1 mol) of 1,4-dihydroxy-2-naphthoic acid and 19 g (0.1 mol) of p-toluenesulfonic acid were added to 200 ml of dehydrated toluene. To the mixture, 27.6 g (0.2 mol) of β-ethylsulfonylethanol was added dropwise for 30 minutes under heating at 95° C. with stirring. After heating with stirring for 7 hours, the mixture was cooled to 20° to 30° C. 100 ml of acetonitrile was added to the mixture, the solid deposited was separated by filtration to obtain 17.2 g (53%) of 1-hydroxy-4-(β-ethylsulfonylethoxy)-2-naphthoic acid. After heating with stirring for 7 hours the mixture was cooled to 20° to 30° C the solid deposited was separated by filtration