Sodium borohydride → 2-Methoxymethoxy-5-(trifluoromethyl)benzyl alcohol

HRID 1081875Notes

Reaction equation

HRID 1081875 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][C:6]=1[CH:7]=[O:8].[BH4-].[Na+]>CO>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:10]([C:13]([F:14])([F:15])[F:16])=[CH:9][C:6]=1[CH2:7][OH:8]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 233631132-(Methoxymethoxy)-5-(trifluoromethyl)benzaldehyde

Product 1

HCID 543883822-Methoxymethoxy-5-(trifluoromethyl)benzyl alcoholYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The solution of 2-methoxymethoxy-5-(trifluoromethyl)benzaldehyde (3.3 g) from Example 59 in anhydrous methanol (20 ml) was cooled in an ice bath, followed by gradual addition of NaBH4 (0.53 g). After stirring at room temperature for 15 minutes, the solvent was removed under reduced pressure. To the residue was added water, and the aqueous layer was extracted with ether. The ether layer was washed with water and saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, to give an colorless oil compound as the title compound (3.15 g; 95%).

Workup

  1. customthe solvent was removed under reduced pressure
  2. additionTo the residue was added water
  3. extractionthe aqueous layer was extracted with ether
  4. washThe ether layer was washed with water and saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-5890f8f66af04e2d9ebcf9b627454dbe
Source dataset
uspto-grants-1996_12
Patent number
US05587392

Reaction notes

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