4-Oxo-6-phenyl-hex-5-enoic acid ethyl ester → 4-Oxo-6-phenylhexanoic acid

HRID 852891Notes

Reaction equation

HRID 852891 reaction equation
C([O:3][C:4](=[O:17])[CH2:5][CH2:6][C:7](=[O:16])[CH:8]=[CH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)C>C(O)C.[Pd]>[O:16]=[C:7]([CH2:8][CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[CH2:6][CH2:5][C:4]([OH:17])=[O:3]

Participants

4

Reactant 1

HCID 694193024-Oxo-6-phenyl-hex-5-enoic acid ethyl ester

Product 1

HCID 6097734-Oxo-6-phenylhexanoic acidYield 94.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 98 (5.0 g, 21 mmol) in ethanol (50 mL) was hydrogenated over 10% Pd—C at 30 psi and room temperature for 4 hr. The catalyst was filtered off and a soluton of NaOH (1 g) in water (10 mL) was added. The solution was stirred for 1 hr then diluted with water and washed with ether. The aqueous solution was acidified with HCl and extracted with ether. The ether extracts were washed with brine, dried over MgSO4 and evaporated to give an oil 4.1 g, 94%.

Workup

  1. filtrationThe catalyst was filtered off
  2. additiona soluton of NaOH (1 g) in water (10 mL) was added
  3. additionthen diluted with water
  4. washwashed with ether
  5. extractionextracted with ether
  6. washThe ether extracts were washed with brine
  7. dry with materialdried over MgSO4
  8. customevaporated

Sources & evidence

ORD record
ord-a5f90e515e1d4af09d9026155f555b6c
Source dataset
uspto-grants-2007_08
Patent number
US07253194B2

Reaction notes

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