1: 100 percent / aq. KOH / methanol / 5 h / Heating 2: 70.42 percent / aq. Na2CO3; NaIO4; KMnO4 / 2-methyl-propan-2-ol / 3 h / Heating View Scheme

1: 1.71 kg / 10percent KOH / methanol / Heating 2: 1.) pyridine, oxalyl chloride / 1.) toluene, RT, 1 h, 2.) toluene, 0.5 h 3: 87 percent / Na2CO3, NaIO4, KMnO4 / 2-methyl-propan-2-ol; H2O / Heating 4: NH3 / ethanol / 8 h / 180 °C 5: H2 / PtO2 / acetic acid / 3 h / 25 - 60 °C / 2327.2 Torr 6: 1.) dimethyl sulfate, 2.) K2CO3 / 1.) CHCl3, reflux, 5 h 7: 1.) LDA / 1.) THF, -78 to 0 deg C, 5 min, 2.) THF 8: 67 mg / NaIO4 / methanol; H2O / 2.5 h 9: toluene / 2.5 h / Heating View Scheme