[CH3:1][O:2][C:3]1([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH2:12][CH2:11][C:6]2(OCC[O:7]2)[CH2:5][CH2:4]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O.C([O-])(O)=O.[Na+]>[F:19][C:16]1[CH:15]=[CH:14][C:13]([C:3]2([O:2][CH3:1])[CH2:4][CH2:5][C:6](=[O:7])[CH2:11][CH2:12]2)=[CH:18][CH:17]=1A solution of 8-(4-fluorophenyl)-1,4-dioxaspiro[4.5]decan-8-ol methyl ether in acetone (200 ml) was stirred for 96 hr with p-toluenesulfonic acid (0.1 g) and the solution diluted with saturated NaHCO3 solution. The mixture was concentrated in vacuo and the residue suspended in water. The mixture was extracted with ether and the ether extracts dried and concentrated in vacuo. The residue was crystallized from hexane to give 4-(4-fluoro-phenyl)-4-methoxycyclohexanone (94%, mp: 57°-59° C.).
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