iodine; oxygen in cyclohexane 3 h; Irradiation;

palladium on activated charcoal T=340 - 350°C; 11 h;

1: 54.38 percent / ammonium acetate, glacial acetic acid / benzene / 12 h / 160 - 165 °C 2: 2) HBr, glacial acetic acid / 1) EtOH, water, r.t., 7 d; 2) reflux, 30 h 3: 86.26 percent / acetic anhydride / Heating 4: 65.72 percent / aluminium chloride / various solvent(s) / a) r.t., overnight, b) 60-65 deg C, 0.5 h 5: 85.19 percent / hydrogen, perchloric acid / Pd-C (10percent) / acetic acid / 50 - 60 °C / 2844.3 Torr 6: 50.38 percent / polyphosphoric acid / 4 h / 100 °C 7: 82.25 percent / LAH / tetrahydrofuran / a) 0 deg C, 2 h, b) reflux, 6 h 8: 16.66 percent / Pd-C (10percent) / 22 h / 380 - 390 °C View Scheme

1: 2) HBr, glacial acetic acid / 1) EtOH, water, r.t., 7 d; 2) reflux, 30 h 2: 86.26 percent / acetic anhydride / Heating 3: 65.72 percent / aluminium chloride / various solvent(s) / a) r.t., overnight, b) 60-65 deg C, 0.5 h 4: 85.19 percent / hydrogen, perchloric acid / Pd-C (10percent) / acetic acid / 50 - 60 °C / 2844.3 Torr 5: 50.38 percent / polyphosphoric acid / 4 h / 100 °C 6: 82.25 percent / LAH / tetrahydrofuran / a) 0 deg C, 2 h, b) reflux, 6 h 7: 16.66 percent / Pd-C (10percent) / 22 h / 380 - 390 °C View Scheme

1: 86.26 percent / acetic anhydride / Heating 2: 65.72 percent / aluminium chloride / various solvent(s) / a) r.t., overnight, b) 60-65 deg C, 0.5 h 3: 85.19 percent / hydrogen, perchloric acid / Pd-C (10percent) / acetic acid / 50 - 60 °C / 2844.3 Torr 4: 50.38 percent / polyphosphoric acid / 4 h / 100 °C 5: 82.25 percent / LAH / tetrahydrofuran / a) 0 deg C, 2 h, b) reflux, 6 h 6: 16.66 percent / Pd-C (10percent) / 22 h / 380 - 390 °C View Scheme

1: 65.72 percent / aluminium chloride / various solvent(s) / a) r.t., overnight, b) 60-65 deg C, 0.5 h 2: 85.19 percent / hydrogen, perchloric acid / Pd-C (10percent) / acetic acid / 50 - 60 °C / 2844.3 Torr 3: 50.38 percent / polyphosphoric acid / 4 h / 100 °C 4: 82.25 percent / LAH / tetrahydrofuran / a) 0 deg C, 2 h, b) reflux, 6 h 5: 16.66 percent / Pd-C (10percent) / 22 h / 380 - 390 °C View Scheme

1: 82.25 percent / LAH / tetrahydrofuran / a) 0 deg C, 2 h, b) reflux, 6 h 2: 16.66 percent / Pd-C (10percent) / 22 h / 380 - 390 °C View Scheme

1: 50.38 percent / polyphosphoric acid / 4 h / 100 °C 2: 82.25 percent / LAH / tetrahydrofuran / a) 0 deg C, 2 h, b) reflux, 6 h 3: 16.66 percent / Pd-C (10percent) / 22 h / 380 - 390 °C View Scheme

1: 85.19 percent / hydrogen, perchloric acid / Pd-C (10percent) / acetic acid / 50 - 60 °C / 2844.3 Torr 2: 50.38 percent / polyphosphoric acid / 4 h / 100 °C 3: 82.25 percent / LAH / tetrahydrofuran / a) 0 deg C, 2 h, b) reflux, 6 h 4: 16.66 percent / Pd-C (10percent) / 22 h / 380 - 390 °C View Scheme

palladium on activated charcoal T=380 - 390°C; 22 h;