Water → 4-(Benzyloxy)-3,5-difluorobenzaldehyde

HRID 1709272Notes

Reaction equation

HRID 1709272 reaction equation
[OH:1][C:2]1[C:9]([F:10])=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[F:11].C(=O)([O-])[O-].[K+].[K+].[CH2:18](Cl)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>CS(C)=O>[CH2:18]([O:1][C:2]1[C:3]([F:11])=[CH:4][C:5]([CH:6]=[O:7])=[CH:8][C:9]=1[F:10])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 101925843,5-Difluoro-4-hydroxybenzaldehyde

Product 1

HCID 157140264-(Benzyloxy)-3,5-difluorobenzaldehyde

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

20 g of 4-hydroxy-3,5-difluorobenzaldehyde are dissolved in dimethylsulfoxide, and potassium carbonate and benzyl chloride are added thereto. After the mixture is stirred at room temperature, water is added thereto. The mixture is extracted with ethyl acetate and evaporated to remove the solvent. The residue is purified by silica gel column chromatography to give 17.4 g of 4-benzyloxy-3,5-difluorobenzaldehyde.

Workup

  1. extractionThe mixture is extracted with ethyl acetate
  2. customevaporated
  3. customto remove the solvent
  4. customThe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7dd0002dc3864c6cb056e52822732410
Source dataset
uspto-grants-1990_08
Patent number
US04948810

Reaction notes

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