Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → methyl(E)-3-(3-butoxy-4-iodophenyl)acrylate

HRID 1361071Notes

Reaction equation

HRID 1361071 reaction equation
C1(P(=[CH:20][C:21]([O:23][CH3:24])=[O:22])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:25]([O:29][C:30]1[CH:31]=[C:32]([CH:35]=[CH:36][C:37]=1[I:38])[CH:33]=O)[CH2:26][CH2:27][CH3:28]>C1(C)C=CC=CC=1>[CH2:25]([O:29][C:30]1[CH:31]=[C:32](/[CH:33]=[CH:20]/[C:21]([O:23][CH3:24])=[O:22])[CH:35]=[CH:36][C:37]=1[I:38])[CH2:26][CH2:27][CH3:28]

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 595749303-Butoxy-4-iodobenzaldehyde

Product 1

HCID 66591222methyl(E)-3-(3-butoxy-4-iodophenyl)acrylateYield 87.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

65.1 g (195 mmol) of methyl (triphenylphosphoranylidene)acetate are added to a solution of 29.6 g (97 mmol) of 3-butoxy-4-iodobenzaldehyde in 360 ml of toluene. The reaction mixture is refluxed for 2 hours. The solvent is evaporated off and the oil obtained is purified by chromatography on a column of silica eluted with a 50/50 heptane/dichloromethane mixture. 30.5 g (87%) of methyl(E)-3-(3-butoxy-4-iodophenyl)acrylate are obtained in the form of pale yellow crystals.

Workup

  1. temperatureThe reaction mixture is refluxed for 2 hours
  2. customThe solvent is evaporated off
  3. customthe oil obtained
  4. customis purified by chromatography on a column of silica
  5. washeluted with a 50/50 heptane/dichloromethane mixture

Sources & evidence

ORD record
ord-91f27634430a4106afab34c7943a2b3c
Source dataset
uspto-grants-2011_02
Patent number
US07879907B2

Reaction notes

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