3-(2-methoxyphenyl)sulfanylpropanal

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

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

Procedure: 4.93 Grams of methyl acetoacetate were dissolved in 7.5 ml of water, and 6.34 g of a 30% aqueous sodium hydroxide solution were added thereto by drops while cooling the mixture to 25° C. or less. After having been stirred at 30°-35° C. for 3 hours, the mixture was adjusted to pH 7.0 with a concentrated aqueous hydrochloric acid solution. Thereafter, 0.30 g of sodium acetate and 1.00 g of tetrabutylammonium bromide were added thereto and then an additional hydrochloric acid was added thereto so that the mixture had a pH of 6.9. Further, 17.8 g of a toluene solution containing 27.5% of 3-(2-methoxyphenylthio)propanal were added thereto and the resulting mixture was stirred at 45°-50° C. for 9 hours. The organic layer was separated from the mixture. It was washed with a 5% aqueous acetic acid solution and then with a saturated aqueous sodium chloride solution. Then it was dried over anhydrous magnesium sulfate. Removing the solvent from the layer under reduced pressure gave 5.78 g of crude 4-hydroxy-6-(2-methoxyphenylthio)-2-hexanone (purity: 79.9%, yield: 75.7%). A purified product was obtained by column chromatography. The purified product had an nD21 of 1.5705. by drops while cooling the mixture to 25° C. or less were added the resulting mixture was stirred at 45°-50° C. for 9 hours The organic layer was separated from the mixture It was washed with a 5% aqueous acetic acid solution Then it was dried over anhydrous magnesium sulfate Removing the solvent from the layer under reduced pressure

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

Procedure: 4.93 Grams of methyl acetoacetate were dissolved in 7.5 ml of water, and 6.34 g of a 30% aqueous sodium hydroxide solution were added thereto by drops while cooling the mixture to 25° C. or less. After having been stirred at 30°-35° C. for 3 hours, the mixture was adjusted to pH 7.0 with a concentrated aqueous hydrochloric acid solution. Thereafter, 0.30 g of sodium acetate and 1.00 g of tetrabutylammonium bromide were added thereto and then an additional hydrochloric acid was added thereto so that the mixture had a pH of 6.9. Further, 17.8 g of a toluene solution containing 27.5% of 3-(2-methoxyphenylthio)propanal were added thereto and the resulting mixture was stirred at 45°-50° C. for 9 hours. The organic layer was separated from the mixture. It was washed with a 5% aqueous acetic acid solution and then with a saturated aqueous sodium chloride solution. Then it was dried over anhydrous magnesium sulfate. Removing the solvent from the layer under reduced pressure gave 5.78 g of crude 4-hydroxy-6-(2-methoxyphenylthio)-2-hexanone (purity: 79.9%, yield: 75.7%). A purified product was obtained by column chromatography. The purified product had an nD21 of 1.5705. by drops while cooling the mixture to 25° C. or less were added the resulting mixture was stirred at 45°-50° C. for 9 hours The organic layer was separated from the mixture It was washed with a 5% aqueous acetic acid solution Then it was dried over anhydrous magnesium sulfate Removing the solvent from the layer under reduced pressure

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

Procedure: 4.93 Grams of methyl acetoacetate were dissolved in 7.5 ml of water, and 6.34 g of a 30% aqueous sodium hydroxide solution were added thereto by drops while cooling the mixture to 25° C. or less. After having been stirred at 30°-35° C. for 3 hours, the mixture was adjusted to pH 7.0 with a concentrated aqueous hydrochloric acid solution. Thereafter, 0.30 g of sodium acetate and 1.00 g of tetrabutylammonium bromide were added thereto and then an additional hydrochloric acid was added thereto so that the mixture had a pH of 6.9. Further, 17.8 g of a toluene solution containing 27.5% of 3-(2-methoxyphenylthio)propanal were added thereto and the resulting mixture was stirred at 45°-50° C. for 9 hours. The organic layer was separated from the mixture. It was washed with a 5% aqueous acetic acid solution and then with a saturated aqueous sodium chloride solution. Then it was dried over anhydrous magnesium sulfate. Removing the solvent from the layer under reduced pressure gave 5.78 g of crude 4-hydroxy-6-(2-methoxyphenylthio)-2-hexanone (purity: 79.9%, yield: 75.7%). A purified product was obtained by column chromatography. The purified product had an nD21 of 1.5705. by drops while cooling the mixture to 25° C. or less were added the resulting mixture was stirred at 45°-50° C. for 9 hours The organic layer was separated from the mixture It was washed with a 5% aqueous acetic acid solution Then it was dried over anhydrous magnesium sulfate Removing the solvent from the layer under reduced pressure

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

Procedure: 4.93 Grams of methyl acetoacetate were dissolved in 7.5 ml of water, and 6.34 g of a 30% aqueous sodium hydroxide solution were added thereto by drops while cooling the mixture to 25° C. or less. After having been stirred at 30°-35° C. for 3 hours, the mixture was adjusted to pH 7.0 with a concentrated aqueous hydrochloric acid solution. Thereafter, 0.30 g of sodium acetate and 1.00 g of tetrabutylammonium bromide were added thereto and then an additional hydrochloric acid was added thereto so that the mixture had a pH of 6.9. Further, 17.8 g of a toluene solution containing 27.5% of 3-(2-methoxyphenylthio)propanal were added thereto and the resulting mixture was stirred at 45°-50° C. for 9 hours. The organic layer was separated from the mixture. It was washed with a 5% aqueous acetic acid solution and then with a saturated aqueous sodium chloride solution. Then it was dried over anhydrous magnesium sulfate. Removing the solvent from the layer under reduced pressure gave 5.78 g of crude 4-hydroxy-6-(2-methoxyphenylthio)-2-hexanone (purity: 79.9%, yield: 75.7%). A purified product was obtained by column chromatography. The purified product had an nD21 of 1.5705. by drops while cooling the mixture to 25° C. or less were added the resulting mixture was stirred at 45°-50° C. for 9 hours The organic layer was separated from the mixture It was washed with a 5% aqueous acetic acid solution Then it was dried over anhydrous magnesium sulfate Removing the solvent from the layer under reduced pressure