Methyl 4-Formylbenzoate → methyl (E)-4-(4-phenyl-1-butenyl)benzoate

HRID 128797Notes

Reaction equation

HRID 128797 reaction equation
[Br-].[C:2]1([CH2:8][CH2:9][CH2:10][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:30]([C:32]1[CH:41]=[CH:40][C:35]([C:36]([O:38][CH3:39])=[O:37])=[CH:34][CH:33]=1)=O>>[C:2]1([CH2:8][CH2:9]/[CH:10]=[CH:30]/[C:32]2[CH:41]=[CH:40][C:35]([C:36]([O:38][CH3:39])=[O:37])=[CH:34][CH:33]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 15294Methyl 4-FormylbenzoateHCID 109286473-Phenylpropyl triphenylphosphonium bromide

Product 1

HCID 14183688methyl (E)-4-(4-phenyl-1-butenyl)benzoate

Procedure

Using the conditions in example 1(A), (3-phenylpropyl)triphenylphosphonium bromide and methyl 4-formylbenzoate are condensed, providing methyl (E)-4-(4-phenyl-1-butenyl)benzoate as a colorless oil after chromatographic separation from the later-eluting (Z) isomer. This is reduced with lithium aluminum hydride in THF in the usual fashion to provide (E)-4-(4-phenyl-1-butenyl)phenylmethanol as a colorless oil. Oxidation with pyridinium dichromate in the usual fashion provides (E)-4-(4-phenyl-1-butenyl)benzaldehyde as a colorless oil after chromatography.

Workup

  1. customcondensed

Sources & evidence

ORD record
ord-9187d2c11d8d4124a796dff270263da5
Source dataset
uspto-grants-1995_11
Patent number
US05464865

Reaction notes

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