1: (i) N2H4*H2O, triethylene glycol, (ii) KOH 2: Na<AlH2(OCH2CH2OMe)2> / benzene / Heating 3: H2SO4, aq. HBr / 6 h / Heating 4: (i) NaOEt, EtOH, (ii) /BRN= 2425374/, (iii) KOH, (iv) (heating) 5: TsOH / CCl4 / Heating 6: (i) Mg, ether, BrCH2CH2Br, (ii) /BRN= 2462934/ 7: (i) TsOH, benzene, (ii) H2, Pt-C View Scheme

1: Na<AlH2(OCH2CH2OMe)2> / benzene / Heating 2: H2SO4, aq. HBr / 6 h / Heating 3: (i) NaOEt, EtOH, (ii) /BRN= 2425374/, (iii) KOH, (iv) (heating) 4: TsOH / CCl4 / Heating 5: (i) Mg, ether, BrCH2CH2Br, (ii) /BRN= 2462934/ 6: (i) TsOH, benzene, (ii) H2, Pt-C View Scheme

1: H2SO4, aq. HBr / 6 h / Heating 2: (i) NaOEt, EtOH, (ii) /BRN= 2425374/, (iii) KOH, (iv) (heating) 3: TsOH / CCl4 / Heating 4: (i) Mg, ether, BrCH2CH2Br, (ii) /BRN= 2462934/ 5: (i) TsOH, benzene, (ii) H2, Pt-C View Scheme

1: (i) NaOEt, EtOH, (ii) /BRN= 2425374/, (iii) KOH, (iv) (heating) 2: TsOH / CCl4 / Heating 3: (i) Mg, ether, BrCH2CH2Br, (ii) /BRN= 2462934/ 4: (i) TsOH, benzene, (ii) H2, Pt-C View Scheme

1: TsOH / CCl4 / Heating 2: (i) Mg, ether, BrCH2CH2Br, (ii) /BRN= 2462934/ 3: (i) TsOH, benzene, (ii) H2, Pt-C View Scheme

1: KOH / methanol; 2-methyl-propan-2-ol 2: (i) N2H4*H2O, triethylene glycol, (ii) KOH 3: Na<AlH2(OCH2CH2OMe)2> / benzene / Heating 4: H2SO4, aq. HBr / 6 h / Heating 5: (i) NaOEt, EtOH, (ii) /BRN= 2425374/, (iii) KOH, (iv) (heating) 6: TsOH / CCl4 / Heating 7: (i) Mg, ether, BrCH2CH2Br, (ii) /BRN= 2462934/ 8: (i) TsOH, benzene, (ii) H2, Pt-C View Scheme

(i) TsOH, benzene, (ii) H2, Pt-C; Multistep reaction;

1: (i) Mg, ether, BrCH2CH2Br, (ii) /BRN= 2462934/ 2: (i) TsOH, benzene, (ii) H2, Pt-C View Scheme