JONES'-reagent; ozone 1.) acetone, tert-butanol, -60 deg C; 2.) acetone, tert-butanol, 0 - 10 deg C, 45 min; Yield given. Multistep reaction;

1: 1.) lithium tri-t-butoxyaluminum hydride, 2.) LAH / 1.)2.) THF, (-68)-(-72) deg C, 1 h 2: 22 percent / pyridine / tetrahydrofuran / Ambient temperature 3: 80 percent / dicyclohexyl carbodiimide, dimethyl sulfoxide, pyridine, trifluoroacetic acid / benzene / 5 h / Ambient temperature 4: 86 percent / KOH / methanol; tetrahydrofuran; H2O / Ambient temperature 5: 1.) conc HCl, 2.) dicyclohexyl carbodiimide, dimethyl sulfoxide, pyridine, trifluoroacetic acid / 1.) methanol, reflux, 2 h; 2.) benzene, r.t., 5 h View Scheme