Hydrochloric Acid → [2-(Benzylsulfanyl)phenyl]methanol

Temperature

0 °C

To a solution of 2-benzylsulfanyl benzoic acid 3 (50 mg, 0.206 mmol) in THF at 0° C. was added LiAlH4 (0.62 mL of a 1.0 mL solution in THF, 0.62 mmol) and the mixture was stirred at 0° C. for 15 minutes then allowed to warm to room temperature. The solution was stirred for 2 hours. The mixture was cooled at 0° C. then methanol (MeOH) was added slowly followed by HCl (0.5N) and tetrahydrofuran (THF). The mixture was stirred at room temperature for 30 minutes. It was then concentrated to remove THF, extracted with CH2Cl2 (3×), dried over MgSO4, filtered and concentrated to give 30 mg of the product as a yellow oil.

1. temperatureto warm to room temperature
2. stirringThe solution was stirred for 2 hours
3. temperatureThe mixture was cooled at 0° C.
4. stirringThe mixture was stirred at room temperature for 30 minutes
5. concentrationIt was then concentrated
6. customto remove THF
7. extractionextracted with CH2Cl2 (3×)
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. concentrationconcentrated

ORD record

ord-7ac90b6a9f3b444691e04f82f4805811

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07935825B2