1: 63 percent / triethylamine / ethanol / 6 h / Heating 2: H2 / Pd/C / ethanol 3: ethanol / 24 h / Ambient temperature 4: MnO2 / acetone / 0.33 h / Ambient temperature 5: aq. HCl; acetone / 0.33 h 6: para-toluenesulfonic acid / toluene / Heating View Scheme

1: H2 / Pd/C / ethanol 2: ethanol / 24 h / Ambient temperature 3: MnO2 / acetone / 0.33 h / Ambient temperature 4: aq. HCl; acetone / 0.33 h 5: para-toluenesulfonic acid / toluene / Heating View Scheme

sodium hydride 1.) 1 h, rt; 2.) 90 deg C, 4 h; Yield given. Multistep reaction. Yields of byproduct given;