Hydrochloric Acid → HCID 14883916, compound

Participants

Reaction Steps

15.10 Grams of methyl acetoacetate were dissolved in 20 ml of water, and 18.20 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, 0.82 g of sodium acetate and 3.22 g of tetrabutylammonium bromide were added thereto and then an additional concentrated aqueous hydrochloric acid solution was added to the mixture so that the mixture was adjusted to pH 6.9. Further, 54.45 g of a toluene solution containing 36.8% of 3-(4-chlorophenylthio)propanal were added thereto and was stirred at 45°-50° C. for 6 hours. The organic layer separated from the layer was washed with a 5% aqueous acetic acid solution and then with a saturated aqueous sodium chloride solution. Then the layer was dried over anhydrous magnesium sulfate. Removing the solvent from the layer under reduced pressure gave 27.08 g of crude 6-(4-chloro-phenylthio)-4-hydroxy-2-hexanone (purity: 87.83%, yield: 92.0%).

Provenance & Evidence