Hydrochloric Acid → 2-Chloro-6-sulfanylbenzoic acid

To a stirred solution of 2.0 grams (0.007 mole) of 6-chloro-2-[ethoxy(thiocarbonyl)thio]benzoic acid in 50 mL of methanol was added 30 ml of aqueous 10% sodium hydroxide. The reaction mixture was warmed to reflux where it stirred for about 18 hours. After this time the reaction mixture was cooled to ambient temperature and was acidified with concentrated hydrochloric acid. The mixture was extracted with ethyl acetate, and the extract was dried with magnesium sulfate. The mixture was filtered, and the filtrate was concentrated under reduced pressure to yield 1.4 grams of 6-chloro-2-mercaptobenzoic acid. The nmr spectrum was consistent with the proposed structure.

1. temperatureThe reaction mixture was warmed
2. temperatureto reflux where it
3. extractionThe mixture was extracted with ethyl acetate
4. dry with materialthe extract was dried with magnesium sulfate
5. filtrationThe mixture was filtered
6. concentrationthe filtrate was concentrated under reduced pressure

ORD record

ord-75137d211a5a4be38a1cac1b8a758ae9

Source dataset

uspto-grants-1992_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05149357