Methanol → (E)-3-phenyl-3-(4-pyridyl)acrylic acid

HRID 744094Notes

Reaction equation

HRID 744094 reaction equation
[OH-].[Na+].CO.[C:5]1(/[C:11](/[C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[CH:12]\[C:13]([O:15]CC)=[O:14])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>O>[C:5]1(/[C:11](/[C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[CH:12]\[C:13]([OH:15])=[O:14])[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 12632077HCID 12632077, compound

Product 1

HCID 67731480(E)-3-phenyl-3-(4-pyridyl)acrylic acidYield 70.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

20 ml of a 10% w/v aqueous solution of sodium hydroxide were added to 35 ml of a methanol solution containing 3.41 g of ethyl (E)-3-phenyl-3-(4-pyridyl)acrylate (prepared as described in Preparation 2), and the mixture was stirred for 1 hour at room temperature. At the end of this time, the reaction solution was poured into 50 ml of water and washed with methylene chloride. Sufficient hydrochloric acid was added to the aqueous phase to adjust the pH to a value of 2.8. The resulting precipitate was collected, giving 2.131 g of the title compound, as a white powder, melting at 239°-241° C.

Workup

  1. washwashed with methylene chloride
  2. additionSufficient hydrochloric acid was added to the aqueous phase
  3. customThe resulting precipitate was collected

Sources & evidence

ORD record
ord-054b42d8fcbe4eca878c96e56e987fb2
Source dataset
uspto-grants-1996_09
Patent number
US05559109

Reaction notes

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