Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → (E,E)-3,3'-(4-Hydroxy-1,3-phenylene)bis-2-propenoic Acid Dimethyl Ester

HRID 1648064Notes

Reaction equation

HRID 1648064 reaction equation
[CH:1]([C:3]1[CH:10]=[C:7]([CH:8]=O)[C:6]([OH:11])=[CH:5][CH:4]=1)=O.C1(P(=[CH:31][C:32]([O:34][CH3:35])=[O:33])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[CH3:35][O:34][C:32](=[O:33])/[CH:31]=[CH:1]/[C:3]1[CH:4]=[CH:5][C:6]([OH:11])=[C:7](/[CH:8]=[CH:31]/[C:32]([O:34][CH3:35])=[O:33])[CH:10]=1

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 1651064-Hydroxyisophthalaldehyde

Product 1

HCID 10706586(E,E)-3,3'-(4-Hydroxy-1,3-phenylene)bis-2-propenoic Acid Dimethyl EsterYield 92.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 5.0 g (33.3 mmol) of 5-formylsalicylaldehyde and 24.5 g (73.3 mmol) of methyl (triphenylphosphoranylidene)acetate, in 150 mL of toluene was stirred and refluxed for 2.5 hr and then kept at room temperature overnight. The solvent was removed in vacuo and the solid residue was flash-chromatographed on silica gel. There was obtained 8.07 g (92.5%) of the title compound as a colorless solid.

Workup

  1. temperaturerefluxed for 2.5 hr
  2. customThe solvent was removed in vacuo
  3. customthe solid residue was flash-chromatographed on silica gel

Sources & evidence

ORD record
ord-8fede513cd3343d6946eca2c2d6cd77c
Source dataset
uspto-grants-1995_07
Patent number
US05434186

Reaction notes

Loading…