4-(Trifluoromethyl)benzaldehyde → 2-Propenoic acid, 3-[4-(trifluoromethyl)phenyl]-, ethyl ester

HRID 2075322Notes

Reaction equation

HRID 2075322 reaction equation
[C:1]([CH:6]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:3][CH2:4][CH3:5])=[O:2].[F:26][C:27]([F:37])([F:36])[C:28]1[CH:33]=[CH:32][C:31]([CH:34]=O)=[CH:30][CH:29]=1>C(Cl)Cl>[F:26][C:27]([F:37])([F:36])[C:28]1[CH:33]=[CH:32][C:31](/[CH:34]=[CH:6]/[C:1]([O:3][CH2:4][CH3:5])=[O:2])=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 679964-(Trifluoromethyl)benzaldehydeHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester

Product 1

HCID 115070152-Propenoic acid, 3-[4-(trifluoromethyl)phenyl]-, ethyl esterYield 71.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (carbethoxymethylene)triphenylphosphorane (55.3 g, 159 mmol) in 150 mL DCM, was added α,α,α-trifluoro-p-tolualdehyde (25.00 g, 144 mmol)(commercially available from 3B Scientific Corporation Product List (Order Number 3B4-3644)) in 75 mL DCM. The reaction was exothermic. The mixture was heated at reflux for 90 minutes. After removing the solvent, hexane was added to the resulting residue. A precipitate appeared and was collected by filtration through filter paper. The collected solid was subjected to silica gel chromatography with 100% hexane as the elutant to afford a white solid ((E)-ethyl 3-(4-(trifluoromethyl)phenyl)acrylate (25.0 g, yield=71%). LCMS (API-ES) m/z(%): 245.1 (100%, M++H); 1H NMR (400 MHz, CD3OD) δ ppm 1.35 (t, J=7.14 Hz, 3H) 4.28 (q, J=7.04 Hz, 2H) 6.68 (d, J=16.04 Hz, 1H) 7.70-7.77 (m, 3H) 7.80-7.84 (m, 2H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 90 minutes
  3. customAfter removing the solvent, hexane
  4. additionwas added to the resulting residue
  5. filtrationwas collected by filtration
  6. filtrationthrough filter paper

Sources & evidence

ORD record
ord-5e4d46ea2501479cb75030cf9f2d22f7
Source dataset
uspto-grants-2011_04
Patent number
US07919504B2

Reaction notes

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