Toluene → HCID 53944768, compound

HRID 728071Notes

Reaction equation

HRID 728071 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:14]=[CH:13][C:10]=1[CH:11]=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:25]([O:27]C(C=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=O)[CH3:26].[C:50]1(C)C=CC=C[CH:51]=1>>[CH2:18]([O:17][C:15]1[CH:16]=[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:51]=[CH:50][C:14]=1[CH:13]=[CH:10][C:11]([O:27][CH2:25][CH3:26])=[O:12])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 3

HCID 1140TolueneHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 18090802,4-Bis(benzyloxy)benzaldehyde

Product 1

HCID 53944768HCID 53944768, compound

Procedure

To a solution of 2,4-dibenzyloxybenzaldehyde (702 mg) in toluene (30 ml), ethoxycarbonylmethylenetriphenylphosphoran (1.0 g) was added, followed by reflux under heating for 2.5 hours. After the reaction mixture was allowed to stand for cooling, the solvent was distilled off and the residue was purified by a silica gel column chromatography. From the fraction eluted with dichloromethane was obtained ethyl 3-(2,4-dibenzyloxyphenyl)-2-propenoate (794 mg) as an oily product.

Workup

  1. temperatureby reflux
  2. temperatureunder heating for 2.5 hours
  3. temperaturefor cooling
  4. distillationthe solvent was distilled off
  5. customthe residue was purified by a silica gel column chromatography
  6. washFrom the fraction eluted with dichloromethane

Sources & evidence

ORD record
ord-61284e26e31b472aa3fcf7e85d7036c2
Source dataset
uspto-grants-1991_09
Patent number
US05047430

Reaction notes

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