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

HRID 250920Notes

Reaction equation

HRID 250920 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.C[C:26]1[C:33]([O:34][CH2:35][CH2:36][CH2:37][CH3:38])=[C:32]([I:39])[CH:31]=[CH:30][C:27]=1[CH:28]=O>C1(C)C=CC=CC=1>[CH2:35]([O:34][C:33]1[CH:26]=[C:27](/[CH:28]=[CH:20]/[C:21]([O:23][CH3:24])=[O:22])[CH:30]=[CH:31][C:32]=1[I:39])[CH2:36][CH2:37][CH3:38]

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 86614974Methyl-3-butoxy-4-iodobenzaldehyde

Product 1

HCID 66591222methyl(E)-3-(3-butoxy-4-iodophenyl)acrylateYield 87.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

65.08 g (0.195 mol, 2 eq) of methyl triphenylphosphoranylideneacetate are added to a solution of 29.60 g (0.097 mol, 1 eq) of methyl-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 chromatographed on silica gel (50/50 heptane/dichloromethane). 30.47 g of methyl (E)-3-(3-butoxy-4-iodophenyl)acrylate are obtained in the form of pale yellow crystals. Yield=87%

Workup

  1. temperatureThe reaction mixture is refluxed for 2 hours
  2. customThe solvent is evaporated off
  3. customthe oil obtained
  4. customis chromatographed on silica gel (50/50 heptane/dichloromethane)

Sources & evidence

ORD record
ord-a19ed6fbdc5e4f27aba7d9bb67898673
Source dataset
uspto-grants-2011_01
Patent number
US07863332B2

Reaction notes

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