Water → 3-Methoxy-4-(2,2,2-trifluoroethoxy)benzaldehyde

HRID 1639012Notes

Reaction equation

HRID 1639012 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH:9]=[O:10])[CH:6]=[CH:5][C:4]=1[OH:11].[H-].[Na+].FC(F)(F)S(O[CH2:20][C:21]([F:24])([F:23])[F:22])(=O)=O.O>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH:6]=[CH:5][C:4]=1[O:11][CH2:20][C:21]([F:24])([F:23])[F:22])[CH:9]=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 1183VanillinHCID 24758Sodium hydrideHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonate

Product 1

HCID 126474993-Methoxy-4-(2,2,2-trifluoroethoxy)benzaldehydeYield 98.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3.96 g of vaniline (e-1) (26.0 mmol) in 26 ml of dry DMF was added 1.04 g of 60% NaH (26.0 mmol) slowly, and the mixture was stirred for 30 min. in a stream of nitrogen. 2,2,2-Trifluoroethyl trifluoromethanesulfonate (6.64 g: 28.6 mmol) was added dropwise to the mixture and stirred overnight at room temperature. The reaction solution was poured into water and extracted with ether. The ether layer was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, eluting with benzene-AcOEt to give 5.98 g of the objective compound 3-methoxy-4-(2,2,2-trifluoroethoxy)benzaldehyde (f-1) (Yield: 98.2%).

Workup

  1. stirringstirred overnight at room temperature
  2. extractionextracted with ether
  3. washThe ether layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washeluting with benzene-AcOEt

Sources & evidence

ORD record
ord-28bdafa80f994560a2261bee49c46726
Source dataset
uspto-grants-1989_11
Patent number
US04882338

Reaction notes

Loading…