sodium hydroxide in ethanol; water 2 h; Heating;

potassium permanganate; sodium hydroxide in water T=143 - 155°C; 5 h;

n-butyllithium; n-butyl-magnesium chloride in tetrahydrofuran; hexane; toluene T=0°C; 0.75 h;

n-butyllithium in diethyl ether; hexane T=-100°C; 0.25 h;

1: 31 percent / t-butylnitrite / dimethylsulfoxide / 1 h 2: 48 percent / H2SO4 / 72 h / Heating View Scheme

1: 1,2,4-tribromo-benzene With isopropylmagnesium chloride in tetrahydrofuran T=-40°C; Grignard reaction; 2 h; 2: carbon dioxide in tetrahydrofuran T=-40°C; 1 h; Further stages. Title compound not separated from byproducts.;

1: 88 percent / diisopropylamine; butyllithium / hexane; tetrahydrofuran / 2 h 2: 92 percent / butyllithium; butylmagnesium chloride / tetrahydrofuran; hexane; toluene / 0.75 h / 0 °C View Scheme

1: 78 percent / butyllithium; 2,2,6,6-tetramethylpiperidine / hexane; tetrahydrofuran / -75 °C 2: 46 percent / Faigl mix / hexane; tetrahydrofuran / 2 h / -100 °C 3: 91 percent / potassium fluoride / tetrahydrofuran; H2O / 12 h / Heating 4: 88 percent / diisopropylamine; butyllithium / hexane; tetrahydrofuran / 2 h 5: 92 percent / butyllithium; butylmagnesium chloride / tetrahydrofuran; hexane; toluene / 0.75 h / 0 °C View Scheme

1: 46 percent / Faigl mix / hexane; tetrahydrofuran / 2 h / -100 °C 2: 91 percent / potassium fluoride / tetrahydrofuran; H2O / 12 h / Heating 3: 88 percent / diisopropylamine; butyllithium / hexane; tetrahydrofuran / 2 h 4: 92 percent / butyllithium; butylmagnesium chloride / tetrahydrofuran; hexane; toluene / 0.75 h / 0 °C View Scheme

1: 91 percent / potassium fluoride / tetrahydrofuran; H2O / 12 h / Heating 2: 88 percent / diisopropylamine; butyllithium / hexane; tetrahydrofuran / 2 h 3: 92 percent / butyllithium; butylmagnesium chloride / tetrahydrofuran; hexane; toluene / 0.75 h / 0 °C View Scheme