Toluene → 4-[(Methylsulfonyl)methyl]benzenemethanol

A 1.0 M solution of diisobutylaluminum hydride in toluene (44 mL, 44 mmol) was added slowly drop-wise to a 0° C. solution of methyl 4-(methanesulfonylmethyl)benzoate (4.00 g, 17.5 mmol) and toluene (220 mL). After the addition was complete, the reaction mixture was warmed to room temperature, then stirred at room temperature for 16 hours. After this time, thin-layer chromatography indicated some starting material to remain. The reaction mixture was cooled to 0° C., then additional 1.0 M diisobutylaluminum hydride in toluene (44 mL, 44 mmol) was added slowly drop-wise to the cold reaction mixture. The reaction mixture was warmed to room temperature, and then stirred for 20 minutes. The reaction mixture was again cooled to 0° C. Ethyl acetate (50 mL) was added followed by methanol (1 mL). The reaction mixture was allowed to stand for 6 minutes at 0° C., during which time the mixture became cloudy and thick. A saturated aqueous solution of sodium potassium tartrate was added, and the heterogeneous mixture was warmed to room temperature. Water and additional ethyl acetate (50 mL) were added. The organic phase was separated, dried over MgSO4, filtered, and concentrated to give 2.18 g (62%) of (4-methane-sulfonylmethyl-phenyl)-methanol as a white solid.

1. additionAfter the addition
2. temperatureThe reaction mixture was cooled to 0° C.
3. temperatureThe reaction mixture was warmed to room temperature
4. stirringstirred for 20 minutes
5. temperatureThe reaction mixture was again cooled to 0° C
6. waitto stand for 6 minutes at 0° C., during which time
7. temperaturethe heterogeneous mixture was warmed to room temperature
8. customThe organic phase was separated
9. dry with materialdried over MgSO4
10. filtrationfiltered
11. concentrationconcentrated

ORD record

ord-a1fc8c7c9177435eac4de7aa95495aab

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08124629B2