1: With sodium hydroxide in water T=100°C; 42 h; 2: With hydrogenchloride in water pH=1;

1: Raney-Ni / ethanol / Heating 2: KOH / aq. ethanol / Heating View Scheme

sodium hydroxide

2: Py / Heating 3: 165 °C / 760000 Torr 4: H2 / Pd-C 5: aq. KOH 6: (i) AgNO3, aq. NaOH, (ii) Br2 7: NaOH View Scheme

1: Py / Heating 2: 165 °C / 760000 Torr 3: H2 / Pd-C 4: aq. KOH 5: (i) AgNO3, aq. NaOH, (ii) Br2 6: NaOH View Scheme

1: aq. KOH 2: (i) AgNO3, aq. NaOH, (ii) Br2 3: NaOH View Scheme

1: (i) AgNO3, aq. NaOH, (ii) Br2 2: NaOH View Scheme

potassium hydroxide in ethanol Heating;

1.1: thionyl chloride / 0 - 20 °C 2.1: N,N,N',N',N'',N''-hexamethylphosphoric triamide; diisopropylamine; n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 - 0 °C / Inert atmosphere 2.2: -78 - 20 °C 3.1: N,N,N',N',N'',N''-hexamethylphosphoric triamide; diisopropylamine; n-butyllithium / hexane; tetrahydrofuran / -78 - 20 °C / Inert atmosphere 4.1: potassium hydroxide; water / methanol / 24 h / Reflux 4.2: pH 3 5.1: sodium hydroxide / water; acetone 6.1: bromine / hexane / 1 h / 20 °C 7.1: sodium hydroxide; water / 24 h / Reflux View Scheme

1.1: N,N,N',N',N'',N''-hexamethylphosphoric triamide; diisopropylamine; n-butyllithium / hexane; tetrahydrofuran / -78 - 20 °C / Inert atmosphere 2.1: potassium hydroxide; water / methanol / 24 h / Reflux 2.2: pH 3 3.1: sodium hydroxide / water; acetone 4.1: bromine / hexane / 1 h / 20 °C 5.1: sodium hydroxide; water / 24 h / Reflux View Scheme