Sodium Hydroxide → (3,4-Bis(difluoromethoxy)phenyl)methanol

HRID 2399401Notes

Reaction equation

HRID 2399401 reaction equation
[F:1][CH:2]([F:16])[O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[O:12][CH:13]([F:15])[F:14])[CH:7]=[O:8].[BH4-].[Na+].[OH-].[Na+]>C(O)C>[F:1][CH:2]([F:16])[O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[O:12][CH:13]([F:15])[F:14])[CH2:7][OH:8]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 145092693,4-Bis(difluoromethoxy)benzaldehyde

Product 1

HCID 53484633(3,4-Bis(difluoromethoxy)phenyl)methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3,4-Bisdifluoromethoxybenzaldehyde (26.2 g, 110 mmol) in absolute ethanol (150 mL) was treated with sodium borohydride (8.32 g, 220 mmol) under an argon atmosphere at room temperature for 0.5 h. Ten percent aqueous sodium hydroxide (130 mL) was added, the ethanol was removed in vacuo, the mixture was partitioned between ether and water and was extracted twice with ether. The organic extract was dried (magnesium sulfate) and evaporated to a pale yellow oil (26.4 g, 100%).

Workup

  1. customthe ethanol was removed in vacuo
  2. customthe mixture was partitioned between ether and water
  3. extractionwas extracted twice with ether
  4. extractionThe organic extract
  5. dry with materialwas dried (magnesium sulfate)
  6. customevaporated to a pale yellow oil (26.4 g, 100%)

Sources & evidence

ORD record
ord-9de5e2df346e4c9c9cecf86fa802887b
Source dataset
uspto-grants-1995_09
Patent number
US05449686

Reaction notes

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