Water → 4-Chloro-3-(methylsulfonyl)benzenemethanol

HRID 1532285Notes

Reaction equation

HRID 1532285 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[C:6]([S:11]([CH3:14])(=[O:13])=[O:12])[CH:5]=1.C([BH-](CC)CC)C.[Li+].O>O1CCCC1>[Cl:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:3][OH:2])=[CH:5][C:6]=1[S:11]([CH3:14])(=[O:12])=[O:13]

Participants

5

Reactant 3

HCID 962WaterHCID 10490815Methyl 4-chloro-3-(methylsulfonyl)benzoateHCID 23664628Lithiumtriethylborohydride2×

Product 1

HCID 537575064-Chloro-3-(methylsulfonyl)benzenemethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 4-chloro-3-(methylsulfonyl)benzoic acid methyl ester (2.4 g) in tetrahydrofuran (50 mL) was added lithium triethylborohydride (1 M in tetrahydrofuran, 24 mL) at 0-5° C. under nitrogen. The mixture was stirred for 30 min and then more of lithium triethylborohydride (1M in tetrahydrofuran, 5 mL) was added and the mixture was further stirred for 60 min. Water (2 mL) was added and the tetrahydrofuran was evaporated under vacuum. Toluene (100 mL) and water (30 mL) were added and then hydrogen peroxide (30% in water, 20 mL) was added at 10-20° C. After 30 min the organic phase was separated and washed with potassium bicarbonate solution (1 M) and then dried with sodium sulphate and evaporated to dryness (yield 1.2 g). 1H-NMR (400 MHz, DMSO-d6) d=3.36 (s, 3H), 4.59 (d, J=5.7 Hz, 2H), 5.52 (t, J=5.7 Hz, 1 H), 7.66 (dd, J=8.2 Hz, 2.1 Hz, 1H), 7.70 (d, J=8.2 Hz, 1H), 8.03 (d, J=2.1 Hz, 1H).

Workup

  1. stirringthe mixture was further stirred for 60 min
  2. customthe tetrahydrofuran was evaporated under vacuum
  3. additionToluene (100 mL) and water (30 mL) were added
  4. additionhydrogen peroxide (30% in water, 20 mL) was added at 10-20° C
  5. customAfter 30 min the organic phase was separated
  6. washwashed with potassium bicarbonate solution (1 M)
  7. dry with materialdried with sodium sulphate
  8. customevaporated to dryness (yield 1.2 g)

Sources & evidence

ORD record
ord-f326fe212bd04ca5af14a734db1a5265
Source dataset
uspto-grants-2001_03
Patent number
US06201027B1

Reaction notes

Loading…