Hydrochloric Acid → HCID 14883917, compound

Participants

Reaction Steps

9.86 Grams of methyl acetoacetate were dissolved in 15 ml of water, and 12.67 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, 0.62 g of sodium acetate and 2.42 g of tetrabutylammonium bromide were added thereto and then an additional concentrated aqueous hydrochloric acid solution was added thereto so that the mixture had a pH of 6.9. Further, 27.4 g of a toluene solution containing 36.6% of 3-(3-fluorophenylthio)butanal were added thereto and the resulting mixture was stirred at 45°-50° C. for 9 hours. The organic layer separated from the mixture 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 12.49 g of crude-6-(3-fluorophenylthio)-4-hydroxy-2-heptanone (purity: 90.8%, yield: 87.4%). A purified product was obtained by column chromatography. The purified product had an nD21 of 1.5342.

Provenance & Evidence