Hydrochloric Acid → HCID 14883923, compound

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, 0.76 g of ammonium acetate and 2.42 g of tetrabutylammonium bromide were added, and then an additional concentrated aqueous hydrochloric acid solution was added thereto so that the mixture was controlled to have a pH of 6.8. Further, 28.00 g of a toluene solution containing 33.6% of 3-(4-methoxyphenylthio)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 12.04 g of crude 4-hydroxy-6-(4-methoxyphenylthio)-2-heptanone (purity: 53.3%, yield: 53.6%). A purified product was obtained by column chromatography. The purified product had an nD21 of 1.5428.

1. temperatureby drops while cooling the mixture to 25° C. or less
2. additionwere added
3. stirringthe resulting mixture was stirred at 45°-50° C. for 9 hours
4. customThe organic layer separated from the mixture
5. washwas washed with a 5% aqueous acetic acid solution
6. dry with materialThen it was dried over anhydrous magnesium sulfate
7. customRemoving the solvent from the layer under reduced pressure

ORD record

ord-295a5278ec1d442397ce7bbbb04f6333

Source dataset

uspto-grants-1992_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05101076