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

HRID 1780829Notes

Reaction equation

HRID 1780829 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-cdfc92e346f04ad490a7a000c3bd4b4c
Source dataset
uspto-grants-1997_05
Patent number
US05631286

Reaction notes

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