1: 50 percent / Ac2O / Heating 2: 41 percent / diethyl ether / reflux, 2 h -> room temperature 3: 28 percent / KF, 18-crown-6-ether / acetonitrile / Heating View Scheme

1: 50 percent / Ac2O / Heating 2: 41 percent / diethyl ether / reflux, 2 h -> room temperature 3: 28 percent / KF, 18-crown-6-ether / acetonitrile / Heating 4: 45 percent / Zn, NH4Cl / aq. ethanol / 5 h / 10 - 15 °C 5: 58 percent / 1 h / Heating View Scheme

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sulfuric acid

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(i) Ac2O, (ii) H2, Raney-Ni; Multistep reaction;

1: (i) Ac2O, (ii) H2, Raney-Ni 2: (i) (chlorination), (ii) NH3 View Scheme