1: 94 percent / sulfuric acid / methanol / 1.) 22 deg C, 24 h, 2.) reflux, 3 h 2: 76 percent / lead tetraacetate / benzene / 0.5 h / 22 °C 3: 82 percent / Jones' reagent / acetone / 0 °C 4: 82 percent / hydrazine hydrate / ethanol; acetone / Heating View Scheme

With  sulfuric acid in  methanol  1.) 22 deg C, 24 h, 2.) reflux, 3 h;   

Multi-step reaction with 2 steps 1: 94 percent / sulfuric acid / methanol / 1.) 22 deg C, 24 h, 2.) reflux, 3 h2: 76 percent / lead tetraacetate / benzene / 0.5 h / 22 °C  

Multi-step reaction with 3 steps 1: 94 percent / sulfuric acid / methanol / 1.) 22 deg C, 24 h, 2.) reflux, 3 h2: 76 percent / lead tetraacetate / benzene / 0.5 h / 22 °C3: 82 percent / Jones' reagent / acetone / 0 °C