Potassium Hydroxide → (E)-3-{4-[(E)-3-(4-hydroxymethyl-phenyl)-3-oxo-propenyl]-phenyl}-acrylic acid

HRID 885845Notes

Reaction equation

HRID 885845 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:11])[CH3:10])=[CH:5][CH:4]=1.[CH:12]([C:14]1[CH:24]=[CH:23][C:17]([CH:18]=[CH:19][C:20]([OH:22])=[O:21])=[CH:16][CH:15]=1)=O.[OH-].[K+]>CCO>[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:11])/[CH:10]=[CH:12]/[C:14]2[CH:15]=[CH:16][C:17](/[CH:18]=[CH:19]/[C:20]([OH:22])=[O:21])=[CH:23][CH:24]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 980772-Propenoic acid, 3-(4-formylphenyl)-HCID 5852641-(4-(Hydroxymethyl)phenyl)ethanone

Product 1

HCID 67049433(E)-3-{4-[(E)-3-(4-hydroxymethyl-phenyl)-3-oxo-propenyl]-phenyl}-acrylic acidYield 67.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-(4-hydroxymethyl-phenyl)-ethanone (1 g, 6.67 mmol), 4-formylcinnamic acid (1.17 g, 6.67 mmol) and 1.7 M KOH (5.89 ml) in EtOH (60 ml) was stirred at room temperature overnight. The resulting precipitate was filtered and washed with EtOH to give 1.39 g of (E)-3-{4-[(E)-3-(4-hydroxymethyl-phenyl)-3-oxo-propenyl]-phenyl}-acrylic acid as its potassium salt.

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with EtOH

Sources & evidence

ORD record
ord-e9b5a30c7af94d5a93f232ae01e1f755
Source dataset
uspto-grants-2012_08
Patent number
US08242175B2

Reaction notes

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