2-(2-Carboxyethenyl)benzoic acid → 3-(2-Carboxyphenyl)propionic acid

HRID 472976Notes

Reaction equation

HRID 472976 reaction equation
[C:1]([CH:4]=[CH:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([OH:10])=[O:9])([OH:3])=[O:2]>CO>[C:1]([CH2:4][CH2:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([OH:10])=[O:9])([OH:3])=[O:2]

Participants

3

Reactant 1

HCID 955172-(2-Carboxyethenyl)benzoic acid

Product 1

HCID 2262943-(2-Carboxyphenyl)propionic acidYield 103%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-(2-carboxyvinyl)benzoic acid (5 g, 26 mmol) in MeOH (45 mL) was bubbled with H2 (10 psi) at room temperature overnight. The mixture was filtered and the filtrate was concentrated to give 2-(2-carboxyethyl)benzoic acid (5.2 g, 100%). 1H-NMR (CDCl3): 2.61 (m, 2H), 3.21 (m, 2H), 7.22 (m, 2H), 7.38 (m, 1H), 7.88 (m, 1H).

Workup

  1. customwas bubbled with H2 (10 psi) at room temperature overnight
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-7353b040683a481c9d25f968b9a66f93
Source dataset
uspto-grants-2014_01
Patent number
US08633212B2

Reaction notes

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