2-Fluoro-4-(trifluoromethyl)benzaldehyde → 2-Methoxy-4-(trifluoromethyl)benzaldehyde

HRID 1021352Notes

Reaction equation

HRID 1021352 reaction equation
F[C:2]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH3:14][O-:15].[Na+]>>[CH3:14][O:15][C:2]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

3

Reactant 2

HCID 5229292-Fluoro-4-(trifluoromethyl)benzaldehydeHCID 10942334Sodium Methoxide

Product 1

HCID 49847042-Methoxy-4-(trifluoromethyl)benzaldehydeYield 85%

Conditions

Temperature
50 °C

Procedure

2-Fluoro-4-(trifluoromethyl)benzaldehyde (5.0 g, 26 mmol) was diluted with sodium methoxide (57 ml of 0.5 M in methanol; 29 mmol), heated to 50° C. and stirred for 6 hours. The reaction was then partially concentrated, diluted with ethyl acetate and water. The layers were separated and the organic layer was dried over MgSO4, filtered and concentrated to yield 2-methoxy-4-(trifluoromethyl)benzaldehyde (4.5 g, 22 mmol, 85% yield).

Workup

  1. concentrationThe reaction was then partially concentrated
  2. additiondiluted with ethyl acetate and water
  3. customThe layers were separated
  4. dry with materialthe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ff1338bb52c9406992717cee2151d985
Source dataset
uspto-grants-2014_05
Patent number
US08716498B2

Reaction notes

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