Water → HCID 22494069, compound

HRID 1816564Notes

Reaction equation

HRID 1816564 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[CH:5]=1.C([Li])CCC.CN(C)[CH:21]=[O:22].O>C(OCC)C>[CH3:1][O:2][CH2:3][C:4]1([CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:11])([F:12])[F:13])[CH2:5]1)[CH:21]=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 149267201-(Methoxymethyl)-3-(trifluoromethyl)benzeneHCID 178418339Butyllithium

Product 1

HCID 22494069HCID 22494069, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

7.0 g of 1-(methoxymethyl)-3-(trifluoromethyl)benzene was dissolved in 300 ml anhydrous diethyl ether, and 19 ml n-butyl lithium (2.5 M solution in hexane) was added dropwise at −78° C. The reaction mixture was stirred at room temperature for 3 hours and cooled again at −78° C., and 10 ml N,N-dimethylformamide was added. The reaction solution was returned to room temperature, poured into water, extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and the solvent was evapoarated. The residue was subjected to silica gel column chromatography, and from fractions eluted with hexane-ethyl acetate (9:1), 5.0 g of 1-(methoxymethyl)-3-(trifluoromethyl)benzaldehyde was obtained as a reddish orange oil.

Workup

  1. temperaturecooled again at −78° C.
  2. customwas returned to room temperature
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. washfrom fractions eluted with hexane-ethyl acetate (9:1)

Sources & evidence

ORD record
ord-468e933b6ee64bee857ce8cee8969f24
Source dataset
uspto-grants-2005_04
Patent number
US06884821B1

Reaction notes

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