Hydrochloric Acid → (2-Chloro-4-methanesulfonyl-phenyl)-methanol

HRID 1254875Notes

Reaction equation

HRID 1254875 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([S:10]([CH3:13])(=[O:12])=[O:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[BH4-].[Na+].Cl>C(O)C>[Cl:1][C:2]1[CH:9]=[C:8]([S:10]([CH3:13])(=[O:11])=[O:12])[CH:7]=[CH:6][C:3]=1[CH2:4][OH:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 27610842-Chloro-4-(methylsulfonyl)benzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 42609245(2-Chloro-4-methanesulfonyl-phenyl)-methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred dispersion of 2-chloro-4-methanesulfonyl-benzaldehyde (25 g, 0.11 mol) in absolute ethanol (120 ml) is added sodium borohydride (4.6 g, 0.12 mol) whilst cooling with an ice-bath to maintain room temperature. After stirring at room temperature for 3 hours, the reaction mixture is poured carefully onto ice-water (600 ml) and acidified to pH 1-2 with 1N HCl. The resulting suspension is extracted with ethyl acetate (400 ml) and the organic portions are combined, washed with brine, dried (MgSO4) and concentrated in vacuo. The resulting crude product is dried in a vacuum oven at 40° C. overnight to yield the titled product which is used crude in the next step.

Workup

  1. temperaturewhilst cooling with an ice-bath
  2. additionthe reaction mixture is poured carefully onto ice-water (600 ml)
  3. extractionThe resulting suspension is extracted with ethyl acetate (400 ml)
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. dry with materialThe resulting crude product is dried in a vacuum oven at 40° C. overnight

Sources & evidence

ORD record
ord-7dac84d079a34844b7151500a080a60b
Source dataset
uspto-grants-2013_06
Patent number
US08455645B2

Reaction notes

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