Hydrochloric Acid → HCID 59834437, compound

Temperature

95 °C

A solution of dimethyl-thiocarbamic acid S-{4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,6-dichloro-phenyl}ester (72) (2.0 g, 3.76 mmol) in ethanol (6.0 mL) was treated with a 3N aqueous potassium hydroxide solution (4.4 mL, 13.2 mmol). The reaction was then heated to 95° C. for 18 h. At this time, the reaction was poured onto water (200 mL), acidified to pH=2 with a 3N aqueous hydrochloric acid solution, and then extracted into methylene chloride (3×100 mL). The organics were washed with water (1×100 mL) and a saturated aqueous sodium chloride solution (1×100 mL), dried with magnesium sulfate, filtered, and concentrated under vacuum. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 80:20 petroleum ether/ethyl acetate) afforded 2-(3,5-dichloro-4-mercapto-phenyl)-ethanol (73) (639 mg, 76%) as a white solid; EI(+)-HRMS m/e calcd for C8H8Cl2OS (M+) 221.9673, found 221.9672. Exact Mass=221.9673; Molecular Weight=223.12

1. additionAt this time, the reaction was poured onto water (200 mL)
2. extractionextracted into methylene chloride (3×100 mL)
3. washThe organics were washed with water (1×100 mL)
4. dry with materiala saturated aqueous sodium chloride solution (1×100 mL), dried with magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated under vacuum

ORD record

ord-3d218947741c4a2fb1148d4eb5f50198

Source dataset

uspto-grants-2010_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07807674B2