Hydrochloric Acid → HCID 20303220, compound

Temperature

50 °C

In a flask (4-isopropylsulfanyl-phenyl)-oxo-acetic acid ethyl ester (4.00 g, 15.85 mmol) was dissolved in toluene (10 mL) and heated to 50° C. in an oil bath. To this heated solution was then added an aqueous sodium hydroxide solution (3 M solution, 6.55 mL, 19.66 mmol) dropwise keeping the temperature of the reaction below 60° C. The reaction was then stirred at 50° C. for 1.5 h. After this time the reaction was removed from the oil bath and concentrated hydrochloric acid (1.52 mL, 18.23 mmol) was added dropwise while the reaction was still at 50° C. It was then allowed to cool to 25° C. and stirred for 16 h. Filter off the solid which turned out to be hygroscopic so the filter paper was washed with methylene chloride and transferred the filterate to a separatory funnel. The aqueous layer was extracted with methylene chloride (3×20 mL) and then the organics were dried over magnesium sulfate, filtered and concentrated in vacuo to afford (4-isopropylsulfanyl-phenyl)-oxo-acetic acid (3.35 g, 94%) as a yellow oily solid (there was a small impurity but the material was carried on without purification).

1. customthe temperature of the reaction below 60° C
2. additionwas added dropwise while the reaction
3. customwas still at 50° C
4. temperatureto cool to 25° C.
5. stirringstirred for 16 h
6. filtrationFilter off the solid which
7. washwas washed with methylene chloride
8. extractionThe aqueous layer was extracted with methylene chloride (3×20 mL)
9. dry with materialthe organics were dried over magnesium sulfate
10. filtrationfiltered
11. concentrationconcentrated in vacuo

ORD record

ord-93c5329761504ba1908e8274f03d45e3

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07935699B2