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

HRID 1503392Notes

Reaction equation

HRID 1503392 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-2028be00a0174faf8bfccaba16dafe14
Source dataset
uspto-grants-2015_12
Patent number
US09212153B2

Reaction notes

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