3-Carbomethoxy-4-(3-methoxyphenyl)-3-butenoic acid → 3-Carbomethoxy-4-(3-methoxyphenyl)butanoic acid

HRID 129693

Reaction equation

HRID 129693 reaction equation
[C:1]([C:5](=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=1)[CH2:6][C:7]([OH:9])=[O:8])([O:3][CH3:4])=[O:2]>C(O)(=O)C.[Pd]>[C:1]([CH:5]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=1)[CH2:6][C:7]([OH:9])=[O:8])([O:3][CH3:4])=[O:2]

Participants

4

Reactant 1

HCID 5896073-Carbomethoxy-4-(3-methoxyphenyl)-3-butenoic acid

Product 1

HCID 106584473-Carbomethoxy-4-(3-methoxyphenyl)butanoic acidYield 83.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 21.1 g (84 mmol) of 3-carbomethoxy-4-(3-methoxyphenyl)-3-butenoic acid in 100 ml of acetic acid with 2.11 g of 10% Pd on carbon is shaken under H2 atmosphere until H2 uptake ceases (approximately 4 hours). This is filtered through celite and the filtrate concentrated in vacuo several times from toluene to afford 17.6 g of 3-carbomethoxy-4-(3-methoxyphenyl)butanoic acid in the form of a yellow oil which is used directly in the next step.

Workup

  1. filtrationThis is filtered through celite
  2. concentrationthe filtrate concentrated in vacuo several times from toluene

Sources & evidence

ORD record
ord-a131f54ab91a46f0a140d8f163f67720
Source dataset
uspto-grants-1995_11
Patent number
US05468898

Linked notes

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