Sodium Hydroxide → HCID 54447167, compound

HRID 2413354Notes

Reaction equation

HRID 2413354 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][C:8]2[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][CH:9]=2)[CH:2]=1.[C:16]([O-:20])(=[O:19])[CH2:17][CH3:18].[Na+].C(OC(=O)CC)(=O)CC.[OH-].[Na+]>>[CH3:18][C:17](=[CH:12][C:11]1[CH:14]=[CH:15][C:8]([O:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[CH:9][CH:10]=1)[C:16]([OH:20])=[O:19]

Participants

5

Reactant 4

HCID 14798Sodium HydroxideHCID 31263Propionic anhydrideHCID 2723816Sodium PropionateHCID 46774194-(Pyridin-3-yloxy)benzaldehyde

Product 1

HCID 54447167HCID 54447167, compoundYield 56%

Procedure

A mixture of 7 g of 4-(3-pyridyloxy)benzaldehyde, 4 g of sodium propionate and 8 ml of propionic anhydride was heated at a temperature of 135° to 140° C. for 2 hours. After allowing the mixture to cool, the mixture was rendered alkaline with an aqueous solution of sodium hydroxide, washed with dichloromethane and rendered acidic with acetic acid. The precipitated crystals were separated by filtration, washed with water and recrystallized from methanol to obtain 5 g (56% yield) of 2-methyl-3-[4-(3-pyridyloxy)phenyl]propenoic acid as colorless prisms having a melting point of 191°-194° C.

Workup

  1. temperaturewas heated at a temperature of 135° to 140° C. for 2 hours
  2. temperatureto cool
  3. washwashed with dichloromethane
  4. customThe precipitated crystals were separated by filtration
  5. washwashed with water
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-05eeeac3d81f4afe8ae40971d95ad14c
Source dataset
uspto-grants-1985_01
Patent number
US04496735

Reaction notes

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