Hydrochloric Acid → 6-(3-Chlorophenylthio)-4-hydroxy-5-methyl-2-hexanone

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, 0.49 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 to the mixture so that the mixture was adjusted to pH 6.8 to 6.9. Further, 27.93 g of a toluene solution containing 38.4% of 3-(3-chlorophenylthio)-2-methylpropanal were added thereto and was stirred at 45°-50° C. for 8 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 the layer was dried over anhydrous magnesium sulfate. Removing the solvent from the layer under reduced pressure gave a crude 6-(3-chlorophenylthio)-4-hydroxy-5-methyl-2-hexanone. A purified product was obtained by column chromatography in a yield of 46.5%. The purified product had an nD21 of 1.5647.

1. temperatureby drops while cooling the mixture to 25° C. or less
2. additionwere added
3. stirringwas stirred at 45°-50° C. for 8 hours
4. customThe organic layer separated from the mixture
5. washwas washed with a 5% aqueous acetic acid solution
6. dry with materialThen the layer was dried over anhydrous magnesium sulfate
7. customRemoving the solvent from the layer under reduced pressure

ORD record

ord-ec34089681164bb992b838604c999256

Source dataset

uspto-grants-1991_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05041679