p-(Trifluoromethoxy)benzaldehyde → 4-(TRIFLUOROMETHOXY)CINNAMIC ALDEHYDE

HRID 379949Notes

Reaction equation

HRID 379949 reaction equation
[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1.C1(P(=[CH:33][CH:34]=[O:35])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:11]=[CH:10][C:7](/[CH:8]=[CH:33]/[CH:34]=[O:35])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 69573p-(Trifluoromethoxy)benzaldehydeHCID 75051(Triphenylphosphoranylidene)acetaldehyde

Product 1

HCID 107511914-(TRIFLUOROMETHOXY)CINNAMIC ALDEHYDEYield 60%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

570 mg (3.0 mmol) of 4-(trifluoromethoxy)benzaldehyde and 913 mg (3.0 mmol) of (triphenylphosphoranylidene)acetaldehyde were heated under reflux in 7.5 ml of toluene under nitrogen atmosphere for 1 hour and 45 minutes. The toluene was distilled off under reduced pressure and the thus obtained residue was purified over column chromatography using 20 g of silica gel. The fractions eluted with a mixed solvent of acetic acid-hexane (1:10) were collected to obtain 387 mg (yield: 60%) of the title compound as an oil.

Workup

  1. distillationThe toluene was distilled off under reduced pressure
  2. customthe thus obtained residue was purified over column chromatography
  3. washThe fractions eluted with a mixed solvent of acetic acid-hexane (1:10)
  4. customwere collected

Sources & evidence

ORD record
ord-724ef7569d8948ac816bd93a5ea8b8c6
Source dataset
uspto-grants-2001_10
Patent number
US06300357B1

Reaction notes

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