3-Methanesulfonylbenzoic acid → (3-Methanesulfonylphenyl)methanol

HRID 858624Notes

Reaction equation

HRID 858624 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8](O)=[O:9])(=[O:4])=[O:3].B.C1COCC1>C1COCC1>[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([CH2:8][OH:9])[CH:11]=[CH:12][CH:13]=1)(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 2203803-Methanesulfonylbenzoic acidHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 23549738(3-Methanesulfonylphenyl)methanolYield 90.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-(methylsulfonyl)benzoic acid (1.0 g, 5.0 mmol) in anhydrous THF (25 mL) was treated with BH3.THF (1 M solution, 7.5 mL) at room temperature. The reaction was stirred for 12 hours before it was quenched by slow addition of MeOH. The solvent was removed and the residue was purified by flash column chromatography (0–5% MeOH in CH2Cl2) to give the product (0.84 g, 90% yield). 1H NMR (300 MHz, CDCl3) δ: 3.06 (s, 3 H), 4.81 (d, J=6.0 Hz, 2 H), 7.54–7.59 (m, 1 H), 7.65–7.68 (m, 1 H), 7.85–7.88 (m, 1 H), 7.96 (s, 1 H).

Workup

  1. customwas quenched by slow addition of MeOH
  2. customThe solvent was removed
  3. customthe residue was purified by flash column chromatography (0–5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-3030ced8d412421fb30859383e95a4c8
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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