Sodium Hydroxide → HCID 54134609, compound

HRID 1780839Notes

Reaction equation

HRID 1780839 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([CH:11]=[CH:12][C:13]=2[O:14][CH:15]([F:17])[F:16])C=O)[CH2:3][CH2:2]1.[BH4-].[Na+].[OH-:20].[Na+]>C(O)C>[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([OH:20])[CH:11]=[CH:12][C:13]=2[O:14][CH:15]([F:17])[F:16])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 189736983-(Cyclopropylmethoxy)-4-(difluoromethoxy)benzaldehyde

Product 1

HCID 54134609HCID 54134609, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Crude 3-cyclopropylmethoxy-4-difluoromethoxybenzaldehyde (26.4 g) in absolute ethanol (200 mL) was treated with sodium borohydride (8.23 g, 217 mmol) under an argon atmosphere at room temperature for 0.33 h. Ten percent aqueous sodium hydroxide (150 mL) was added, the ethanol was removed in vacuo and the aqueous residue was extracted three times with ether. The organic extract was washed twice with brine, was dried (sodium sulfate), was filtered and was evaporated to a pale yellow oil (24.4 g).

Workup

  1. customthe ethanol was removed in vacuo
  2. extractionthe aqueous residue was extracted three times with ether
  3. extractionThe organic extract
  4. washwas washed twice with brine
  5. dry with materialwas dried (sodium sulfate)
  6. filtrationwas filtered
  7. customwas evaporated to a pale yellow oil (24.4 g)

Sources & evidence

ORD record
ord-4456a194c8a0409daf7209caa3d8ab35
Source dataset
uspto-grants-1997_05
Patent number
US05631286

Reaction notes

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