3-(Trifluoromethyl)benzaldehyde → (2E)-3-(3-(trifluoromethyl)phenyl)prop-2-enal

HRID 1257304Notes

Reaction equation

HRID 1257304 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=O.C1(P(=[CH:32][CH:33]=[O:34])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5](/[CH:6]=[CH:32]/[CH:33]=[O:34])[CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 679903-(Trifluoromethyl)benzaldehydeHCID 75051(Triphenylphosphoranylidene)acetaldehyde

Product 1

HCID 10488238(2E)-3-(3-(trifluoromethyl)phenyl)prop-2-enalYield 51.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-(Trifluoromethyl)benzaldehyde (0.70 g) was dissolved in toluene (16 mL), and (triphenylphosphoranylidene)acetoaldehyde (1.22 g) was added. The reaction mixture was heated under reflux for 40 hr and concentrated, and the residue was purified by column chromatography (carrier: silica gel, eluent: hexane-ethyl acetate) to give the title compound (0.41 g) as an oil.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 40 hr
  3. concentrationconcentrated
  4. customthe residue was purified by column chromatography (carrier: silica gel, eluent: hexane-ethyl acetate)

Sources & evidence

ORD record
ord-cd80c6a0bba347869be0533b44a11e18
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

Loading…