Hydrochloric Acid → [[2-[(4-Hydroxyphenyl)thio]ethyl]thio]acetic acid

Mercaptoacetic acid (3.5 g, 0.039 mole) was added to ethyl alcohol (100 ml) containing sodium (1.8 g, 0.078 mole). The compound of Example 36 (7.3 g, 0.039 mole) in ethyl alcohol (20 ml) was added dropwise and the mixture refluxed 1 hour. The reaction mixture was cooled to room temperature, poured into water (250 ml) and acidified with 2N hydrochloric acid. The product was extracted into ethyl ether (2×150 ml) and the ethyl ether extracted with 1M sodium bicarbonate (3×80 ml). The combined basic washes were acidified with 2N hydrochloric acid and extracted with ethyl ether (3×150 ml). The combined ethyl ether extracts were washed with water (3×75 ml) and saturated sodium chloride (50 ml), dried over magnesium sulfate, filtered and concentrated to give yellow solid. Recrystallization from ethyl ether/pentane gave the title compound, m.p. ca. 105° C.

1. temperaturethe mixture refluxed 1 hour
2. extractionThe product was extracted into ethyl ether (2×150 ml)
3. extractionthe ethyl ether extracted with 1M sodium bicarbonate (3×80 ml)
4. extractionextracted with ethyl ether (3×150 ml)
5. washThe combined ethyl ether extracts were washed with water (3×75 ml) and saturated sodium chloride (50 ml)
6. dry with materialdried over magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated
9. customto give yellow solid
10. customRecrystallization from ethyl ether/pentane

ORD record

ord-5e0bc2d09bf44feab8b2126fcd11b5bb

Source dataset

uspto-grants-1988_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04755524