[CH3:1][C:2]1[CH:7]([CH2:8][CH2:9][C:10]([CH3:12])=[O:11])[C:6]([CH3:14])([CH3:13])[CH2:5][CH2:4][CH:3]=1.P([O-])(O)(O)=O.[K+].[Cl:21][O-].[Na+].C(O)(=O)C>C(Cl)Cl.O>[Cl:21][CH:3]1[CH2:4][CH2:5][C:6]([CH3:14])([CH3:13])[CH:7]([CH2:8][CH2:9][C:10](=[O:11])[CH3:12])[C:2]1=[CH2:1]
388 g (2 mol) of dihydro-α-ionone was placed in 2.2 l of methylene chloride in a 10 l four-necked flask fitted with a stirrer, thermometer, condenser and dropping funnel. Then, 660 g (4.6 mol) of potassium dihydrogen phosphate dissolved in 3 l of water was added and the resulting emulsion was cooled in an ice bath. 1.6 (2.3 mol) of sodium hypochlorite solution (~12%) was added at about 10° within 1.5 hours and, after about 3 hours at 15°, a further 350 ml (0.5 mol) was added. The pH value of the mixture was adjusted to ~5.5 with acetic acid and it was stirred at room temperature. After a total reaction time of 27 hours the phases were separated and the aqueous phase was extracted 4 times with methylene chloride. The combined organic phases were washed neutral once with water, twice with saturated NaHCO3 solution and a further 3 times with water, dried over MgSO4, filtered and evaporated (bath temperature=room temperature). 407.45 g 4-(3-chloro-2-methylidene-6,6-dimethyl-cyclohex-1-yl)-butan-2-one was obtained as a yellow liquid.
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