4-Oxo-6-phenyl-hex-5-enoic acid ethyl ester → 4-Oxo-6-phenylhexanoic acid
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
Product 1
Reagents, catalysts & solvents 2
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%.