Sodium Hydroxide → 2-Propenoic acid, 3-(4-nitrophenyl)-

HRID 1368886Notes

Reaction equation

HRID 1368886 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH:11][C:12]([O:14]CC)=[O:13])=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH-].[Na+]>O1CCOCC1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:10]=[CH:11][C:12]([OH:14])=[O:13])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 95370Ethyl 3-(4-nitrophenyl)-2-propenoate

Product 1

HCID 701562-Propenoic acid, 3-(4-nitrophenyl)-Yield 60.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The ethyl 3-(4-nitrophenyl)acrylate (512.8 mg) obtained in the above step (a) was dissolved in dioxane (5.1 ml), and the solution was added with 5 N sodium hydroxide (2.78 ml) and stirred at room temperature for 3.5 hours. Separation and extraction with diethyl ether was made to remove impurities, and then 5 N hydrochloric acid was added to the aqueous layer to reduce the pH to 2. The precipitated crystals were collected by filtration to obtain 3-(4-nitrophenyl)acrylic acid (270.1 mg, 60.3%).

Workup

  1. customSeparation and extraction with diethyl ether
  2. customto remove impurities
  3. addition5 N hydrochloric acid was added to the aqueous layer
  4. filtrationThe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-e54ea91076934d4cb49f6f1810997b2c
Source dataset
uspto-grants-2003_06
Patent number
US06576627B1

Reaction notes

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