Hydrochloric Acid → Benzoic acid, 3-mercapto-

To a suspension of 3-(chlorosulfonyl)benzoic acid (22.0 g, 0.10 mol) and zinc powder (87.5 g, 1.3 mol) in benzene (150 mL) was added at 0° C., in a dropwise manner, concentrated hydrochloric acid (150 mL, 10 M). The mixture was heated at reflux, stirred for 1 hour, cooled to room temperature, and filtered through a pad of celite, which was subsequently washed with benzene (3×50 mL). The organic layer was separated and washed with water (100 mL), and brine (100 mL), dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to give a white solid which was recrystallised from aqueous ethanol (9.5 g, 62%) to give the title compound as a solid, mp 147° C.

1. temperatureThe mixture was heated
2. temperatureat reflux
3. filtrationfiltered through a pad of celite, which
4. washwas subsequently washed with benzene (3×50 mL)
5. customThe organic layer was separated
6. washwashed with water (100 mL), and brine (100 mL)
7. dry with materialdried over anhydrous MgSO4
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure
10. customto give a white solid which
11. customwas recrystallised from aqueous ethanol (9.5 g, 62%)

ORD record

ord-bbe7326d08aa452ab08417799f2eba99

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07683185B2