4-Acetoxy-3-phenyl-but-2-enoic acid methyl ester → 4-Acetoxy-3-phenyl-butyric Acid Methyl Ester

HRID 8190Notes

Reaction equation

HRID 8190 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH:4]=[C:5]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:6][O:7][C:8](=[O:10])[CH3:9]>[Pd].C(O)(=O)C>[CH3:1][O:2][C:3](=[O:17])[CH2:4][CH:5]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:6][O:7][C:8](=[O:10])[CH3:9]

Participants

4

Reactant 1

HCID 693648894-Acetoxy-3-phenyl-but-2-enoic acid methyl ester

Product 1

HCID 693657724-Acetoxy-3-phenyl-butyric Acid Methyl EsterYield 92.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 4-acetoxy-3-phenyl-but-2-enoic acid methyl ester, (1.0 g, 4.27 mmol), 10 wt. % palladium on activated carbon (1.0 g), acetic acid (10 mL) is shaken under an atmosphere of hydrogen on a Parr® Shaker. The mixture is filtered through a pad of Celite® and rinsed with methanol. The solution is concentrated in vacuo to yield 0.93 g (92%) of the title compound.

Workup

  1. filtrationThe mixture is filtered through a pad of Celite®
  2. washrinsed with methanol
  3. concentrationThe solution is concentrated in vacuo

Sources & evidence

ORD record
ord-2d0268180b8e432b931028249aef5399
Source dataset
uspto-grants-2006_08
Patent number
US07087626B2

Reaction notes

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