3-Methanesulfonylbenzoic acid → (3-Methanesulfonylphenyl)methanol

Temperature

0 °C

To an ice-cold solution of 3-(methylsulfonyl)benzoic acid (1.4 g, 7.1 mmol) in 2:1 Et2O/THF (60 mL) was added LiAlH4 (8.5 mL of 1.0 M solution in THF, 8.5 mmol), and the reaction mixture was heated at reflux for 1 h. The reaction mixture was cooled to 0° C., and the reaction was quenched with water (15 mL) and 15% NaOH in water (35 mL). The reaction mixture was filtered, concentrated under reduced pressure, and the residue was dissolved in EtOAc. The organic solution was washed with water and then brine, dried (MgSO4), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica, eluent 1:2 to 3:1 EtOAc/hexanes) provided (3-methanesulfonyl)phenyl methanol as a clear oil (0.56 g, 42%): 1H NMR (300 MHz, CDCl3) δ 7.93 (s, 1H), 7.83 (d, J=7 Hz, 1H), 7.64 (d, J=7 Hz, 1H), 7.53 (t, J=7 Hz, 1H), 4.78 (d, J=6 Hz, 2H), 3.05 (s, 3H), 2.61 (br s, 1H). Step 2. Preparation of 1-Chloromethyl-3-methanesulfonylbenzene.

1. temperaturethe reaction mixture was heated
2. temperatureat reflux for 1 h
3. customthe reaction was quenched with water (15 mL) and 15% NaOH in water (35 mL)
4. filtrationThe reaction mixture was filtered
5. concentrationconcentrated under reduced pressure
6. dissolutionthe residue was dissolved in EtOAc
7. washThe organic solution was washed with water
8. dry with materialbrine, dried (MgSO4)
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure
11. customPurification by flash column chromatography (silica, eluent 1:2 to 3:1 EtOAc/hexanes)

ORD record

ord-7d0dbbb2c6ba45af9596ac9eaab5746e

Source dataset

uspto-grants-2006_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07067540B2