[CH2:1]([CH:3]([CH2:6][CH3:7])[CH:4]=O)[CH3:2].[CH3:8][C:9](=[O:12])[CH:10]=[CH2:11].S(=O)(=O)(O)O.C(=O)([O-])O.[Na+]>C1C=CC=CC=1.C(OCC)(=O)C>[CH2:1]([C:3]1([CH2:6][CH3:7])[CH2:4][CH2:8][C:9](=[O:12])[CH:10]=[CH:11]1)[CH3:2]In 75 ml of benzene was dissolved 15.0 g of 2-ethylbutanal, to which were added 10.5 g of 3-buten-2-one and 0.15 ml of concentrated sulfuric acid at ambient temperature. While heating the mixture under reflux, an azeotropic distillation treatment was carried out for 3 hours by means of Dean Stark apparatus. The reaction mixture was poured into a mixture of ice water and ethyl acetate, pH was adjusted to 7.0 with a saturated aqueous solution of sodium hydrogen carbonate, and the organic layer was separated. The organic layer was washed successively with water and saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. Purification of the residue by distillation under reduced pressure gave 4.90 g of 4,4-diethyl-2-cyclohexen-1-one as a light yellow oily product.
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