Carbon Dioxide → 4-Acetylbutyric acid
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ON1[C:6](=O)[CH2:5][CH2:4][C:3]1=[O:8].[CH3:9]C1CCCC=1.[C:15](=[O:17])=[O:16].O=O>C(O)(=O)C.O.O.O.O.C([O-])(=O)C.[Co+2].C([O-])(=O)C>[O:8]=[C:3]([CH3:9])[CH2:4][CH2:5][CH2:6][C:15]([OH:17])=[O:16]ON1[C:6](=O)[CH2:5][CH2:4][C:3]1=[O:8].[CH3:9]C1CCCC=1.[C:15](=[O:17])=[O:16].O=O>C(O)(=O)C.O.O.O.O.C([O-])(=O)C.[Co+2].C([O-])(=O)C>[O:8]=[C:3]([CH3:9])[CH2:4][CH2:5][CH2:6][C:15]([OH:17])=[O:16]
This reaction was performed with a solution of 0.1191 g (1.03 mmol) of N-hydroxysuccinimide, 2.0 g (24.3 mmol) of 1-methylcyclopentene and 0.1330 g (0.53 mmol) of cobalt acetate tetrahydrate in 40 ml of acetic acid was heated to 100° C. in a Parr Hastelloy reactor with temperature and pressure transducer. After the temperature reached 100° C., 745 psi of CO2 was introduced into the reactor, then 120 psi of O2 was added slowly to the reactor. The mixture was stirred under pressure for one hour at 100° C., then the pressure was released, and the mixture was cooled to room temperature. The solution was extracted with ethyl acetate then with a saturated NaCl solution in water and, dried over Na2SO4 to give, as the major 60% 5-ketohexanoic acid.
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