1: With sodium hydroxide in methanol; water T=60°C; 9 h; 2: With hydrogenchloride in water pH=3;

1: 1-fluoro-4-[(methoxymethoxy)methyl]benzene With N,N,N',N'',N''-pentamethyldiethylenetriamine; sec.-butyllithium in tetrahydrofuran; cyclohexane T=-75°C; 2 h; 2: carbon dioxide in tetrahydrofuran; cyclohexane Further stages.;

1: 1-fluoro-4-hydroxymethylbenzene With N,N,N',N'',N''-pentamethyldiethylenetriamine; potassium tert-butylate; sec.-butyllithium in tetrahydrofuran; cyclohexane T=-75°C; 2 h; 2: carbon dioxide in tetrahydrofuran; cyclohexane Further stages.;

1.1: 68 percent / N-ethyldiisopropylamine / CH2Cl2 / 2 h / 25 °C 2.1: sec-butyllithium; N,N,N',N",N"-pentamethyldiethylenetriamine / tetrahydrofuran; cyclohexane / 2 h / -75 °C 2.2: 56 percent / tetrahydrofuran; cyclohexane View Scheme

water in methanol Alkaline conditions;

sulfuric acid 18 h; Heating / reflux;