1: 72 percent / AcOH / ethanol / 2.5 h / Heating 2: 1) p-TsOH*H2O / 1) benzene, reflux, 1 h; 2) ether 3: 9.5 g / aq. 5 percent HCl, acetone / 1 h / Heating 4: 13.5 g / p-TsOH*H2O / benzene / 1 h / Heating 5: 1) LiAlH4; 2) EtOAc, water, aq. 4 N NaOH / 1) THF, 1 h; 2) RT, 1 h 6: 99 percent / tri-n-butylphosphine / pyridine / 23 h / 60 °C 7: 1) aq. NaHCO3, 80 percent m-chloroperbenzoic acid; 2) aq. 10 percent Na2S2O3 / 1) RT, CH2Cl2, 1 h 8: 4.63 g / aq. 5 percent HCl, acetone / 1.5 h / Heating 9: p-TsOH*H2O / benzene / 0.5 h / Heating View Scheme

1: 1) p-TsOH*H2O / 1) benzene, reflux, 1 h; 2) ether 2: 9.5 g / aq. 5 percent HCl, acetone / 1 h / Heating 3: 13.5 g / p-TsOH*H2O / benzene / 1 h / Heating 4: 1) LiAlH4; 2) EtOAc, water, aq. 4 N NaOH / 1) THF, 1 h; 2) RT, 1 h 5: 99 percent / tri-n-butylphosphine / pyridine / 23 h / 60 °C 6: 1) aq. NaHCO3, 80 percent m-chloroperbenzoic acid; 2) aq. 10 percent Na2S2O3 / 1) RT, CH2Cl2, 1 h 7: 4.63 g / aq. 5 percent HCl, acetone / 1.5 h / Heating 8: p-TsOH*H2O / benzene / 0.5 h / Heating View Scheme

1: 13.5 g / p-TsOH*H2O / benzene / 1 h / Heating 2: 1) LiAlH4; 2) EtOAc, water, aq. 4 N NaOH / 1) THF, 1 h; 2) RT, 1 h 3: 99 percent / tri-n-butylphosphine / pyridine / 23 h / 60 °C 4: 1) aq. NaHCO3, 80 percent m-chloroperbenzoic acid; 2) aq. 10 percent Na2S2O3 / 1) RT, CH2Cl2, 1 h 5: 4.63 g / aq. 5 percent HCl, acetone / 1.5 h / Heating 6: p-TsOH*H2O / benzene / 0.5 h / Heating View Scheme

1: 94 percent / aq. 2 N NaOH, hexadecyltributylphosphonium bromide / benzene / 72 h / Heating 2: 1) aq. 5 percent NaHCO3, 80 percent m-chloroperbenzoic acid; 2) aq. 10 percent Na2S2O3 / 1) RT, CH2Cl2, 1 h View Scheme

1: 100 percent / p-TsOH*H2O / benzene / 0.5 h / Heating 2: 94 percent / aq. 2 N NaOH, hexadecyltributylphosphonium bromide / benzene / 72 h / Heating 3: 1) aq. 5 percent NaHCO3, 80 percent m-chloroperbenzoic acid; 2) aq. 10 percent Na2S2O3 / 1) RT, CH2Cl2, 1 h View Scheme

1: 9.5 g / aq. 5 percent HCl, acetone / 1 h / Heating 2: 13.5 g / p-TsOH*H2O / benzene / 1 h / Heating 3: 1) LiAlH4; 2) EtOAc, water, aq. 4 N NaOH / 1) THF, 1 h; 2) RT, 1 h 4: 99 percent / tri-n-butylphosphine / pyridine / 23 h / 60 °C 5: 1) aq. NaHCO3, 80 percent m-chloroperbenzoic acid; 2) aq. 10 percent Na2S2O3 / 1) RT, CH2Cl2, 1 h 6: 4.63 g / aq. 5 percent HCl, acetone / 1.5 h / Heating 7: p-TsOH*H2O / benzene / 0.5 h / Heating View Scheme

1: 1) aq. NaHCO3, 80 percent m-chloroperbenzoic acid; 2) aq. 10 percent Na2S2O3 / 1) RT, CH2Cl2, 1 h 2: 4.63 g / aq. 5 percent HCl, acetone / 1.5 h / Heating 3: p-TsOH*H2O / benzene / 0.5 h / Heating View Scheme

1: 99 percent / tri-n-butylphosphine / pyridine / 23 h / 60 °C 2: 1) aq. NaHCO3, 80 percent m-chloroperbenzoic acid; 2) aq. 10 percent Na2S2O3 / 1) RT, CH2Cl2, 1 h 3: 4.63 g / aq. 5 percent HCl, acetone / 1.5 h / Heating 4: p-TsOH*H2O / benzene / 0.5 h / Heating View Scheme

toluene-4-sulfonic acid in benzene 0.5 h; Heating; Yield given;

sodium hydrogencarbonate; sodium thiosulfate; 3-chloro-benzenecarboperoxoic acid 1) RT, CH2Cl2, 1 h; Yield given. Multistep reaction;