sodium acetate; acetic acid; hydroquinone in water T=220°C; 17 h;

1: 86 percent / n-BuLi / tetrahydrofuran; hexane / Ambient temperature; 1.) 3 h, 2.) overnight 2: 41 percent / Jones reagent / acetone / 5 °C 3: 93 percent / 60 percent HBr / acetic acid / 6 h / Heating 4: 88 percent / CH3COOH, CH3COONa, hydroquinone / H2O / 17 h / 220 °C View Scheme

1: 41 percent / Jones reagent / acetone / 5 °C 2: 93 percent / 60 percent HBr / acetic acid / 6 h / Heating 3: 88 percent / CH3COOH, CH3COONa, hydroquinone / H2O / 17 h / 220 °C View Scheme

1: 93 percent / 60 percent HBr / acetic acid / 6 h / Heating 2: 88 percent / CH3COOH, CH3COONa, hydroquinone / H2O / 17 h / 220 °C View Scheme

1: 86 percent / n-BuLi / tetrahydrofuran; hexane / Ambient temperature; 1.) 3 h, 2.) overnight 2: 41 percent / Jones reagent / acetone / 5 °C 3: 93 percent / 60 percent HBr / acetic acid / 6 h / Heating 4: 88 percent / CH3COOH, CH3COONa, hydroquinone / H2O / 17 h / 220 °C View Scheme