Hydrochloric Acid → (4-(Methylsulfonyl)-2-(trifluoromethyl)phenyl)methanol

HRID 1364579Notes

Reaction equation

HRID 1364579 reaction equation
[CH3:1][S:2]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[C:7]([C:13]([F:16])([F:15])[F:14])[CH:6]=1)(=[O:4])=[O:3].[BH4-].[Na+].Cl>CCO>[CH3:1][S:2]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][OH:10])=[C:7]([C:13]([F:14])([F:15])[F:16])[CH:6]=1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 513420184-Methanesulfonyl-2-(trifluoromethyl)benzaldehyde

Product 1

HCID 66936507(4-(Methylsulfonyl)-2-(trifluoromethyl)phenyl)methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 4-methanesulfonyl-2-trifluoromethyl-benzaldehyde (49.2 g, 0.20 mol) in dry EtOH (500 ml), cooled in an ice-bath, is added sodium borohydride (10.8 g, 0.22 mol), portionwise over 30 mins. The reaction mixture is allowed to warm up slowly to room temperature then stirring is continued for 16 h. The reaction mixture is poured into a beaker of crushed ice (700 ml) and adjusted to pH 1 with 2N HCl (approx. 200 ml). The resulting pale yellow suspension is extracted with CH2Cl2 (3×150 ml), dried (MgSO4) and evaporated to dryness in vacuo. to afford a pale yellow solid.

Workup

  1. temperaturecooled in an ice-bath
  2. waitis continued for 16 h
  3. extractionThe resulting pale yellow suspension is extracted with CH2Cl2 (3×150 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated to dryness in vacuo
  6. customto afford a pale yellow solid

Sources & evidence

ORD record
ord-73aca806d3dc47a1b52b33f1efaadbaf
Source dataset
uspto-grants-2011_02
Patent number
US07888383B2

Reaction notes

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