Water → 2-(Methoxymethoxy)-5-(trifluoromethyl)benzaldehyde

HRID 1081874Notes

Reaction equation

HRID 1081874 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][CH:6]=1.[Li]CCCC.CN([CH:23]=[O:24])C.O>CCOCC>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:12])([F:13])[F:14])=[CH:7][C:6]=1[CH:23]=[O:24]

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 110090761-(Methoxymethoxy)-4-(trifluoromethyl)benzeneHCID 178418339Butyllithium

Product 1

HCID 233631132-(Methoxymethoxy)-5-(trifluoromethyl)benzaldehydeYield 79%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To the solution of 4-(trifluoromethyl)phenyl methoxymethyl ether (5 g) in anhydrous ether (50 ml) was gradually added dropwise 1.6M n-BuLi (16.7 ml) at room temperature. After stirring at room temperature for 2 hours, the solution of DMF (4.13 ml) in anhydrous ether (20 ml) was added dropwise over 30 minutes, and the solution was stirred for 1 hour. To the reaction solution was added water, and the ether layer was separated. The ether layer is was washed with water and saturated sodium chloride solution, and dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified by chromatography on a silica gel column (methylene chloride:hexane=1:1), to give the title compound (4.49 g; 79%).

Workup

  1. stirringthe solution was stirred for 1 hour
  2. customthe ether layer was separated
  3. washThe ether layer is was washed with water and saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe resulting residue was purified by chromatography on a silica gel column (methylene chloride:hexane=1:1)

Sources & evidence

ORD record
ord-405fa717f88f46a289474d2af6aa8292
Source dataset
uspto-grants-1996_12
Patent number
US05587392

Reaction notes

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