1: H2 / 5percent Pd/C / toluene / 1 h / 760 Torr / Ambient temperature 2: toluene / 3 h / Heating 3: 5percent Pd/C / toluene / 1.5 h / Heating 4: 45 percent / benzyltributylammonium chloride, 1 N aq. NaOH / CH2Cl2 / 10 h 5: 10percent aq. NaOH / methanol / 1.5 h / Heating View Scheme

1: toluene / 3 h / Heating 2: 5percent Pd/C / toluene / 1.5 h / Heating 3: 45 percent / benzyltributylammonium chloride, 1 N aq. NaOH / CH2Cl2 / 10 h 4: 10percent aq. NaOH / methanol / 1.5 h / Heating View Scheme

1: 76 percent / H2O / 0.5 h / 40 °C 2: H2 / 5percent Pd/C / toluene / 1 h / 760 Torr / Ambient temperature 3: toluene / 3 h / Heating 4: 5percent Pd/C / toluene / 1.5 h / Heating 5: 45 percent / benzyltributylammonium chloride, 1 N aq. NaOH / CH2Cl2 / 10 h 6: 10percent aq. NaOH / methanol / 1.5 h / Heating View Scheme

sodium hydroxide in methanol 1.5 h; Heating; Yield given;

1: 45 percent / benzyltributylammonium chloride, 1 N aq. NaOH / CH2Cl2 / 10 h 2: 10percent aq. NaOH / methanol / 1.5 h / Heating View Scheme