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

HRID 2109737Notes

Reaction equation

HRID 2109737 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, alpha,alpha,alpha-trifluoro-p-tolualdehyde (25.00 g, 144 mmol) in 75 mL DCM was added. The reaction is 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 filtered through filter paper. The collected solid was subjected to a silica gel chromatography with 100% hexane as the eluant 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=1 6.04 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 filtered
  6. filtrationthrough filter paper

Sources & evidence

ORD record
ord-2e52fa49772b4e63aaa9367038a8a0e7
Source dataset
uspto-grants-2009_04
Patent number
US07514566B2

Reaction notes

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