hydrogenchloride; sodium nitrite in water

1: 1-chloro-3-(methoxymethoxy)benzene With n-butyllithium in tetrahydrofuran; hexane T=-75°C; 2 h; 2: carbon dioxide in tetrahydrofuran; hexane 3: With hydrogenchloride in water pH=1; Title compound not separated from byproducts;

1.1: 55 percent / N-ethyldiisopropylamine / CH2Cl2 / 2 h / 25 °C 2.1: butyllithium / tetrahydrofuran; hexane / 2 h / -75 °C 2.2: tetrahydrofuran; hexane 2.3: HCl / H2O / pH 1 View Scheme

1.1: 2,2,6,6-tetramethylpiperidine; butyllithium / tetrahydrofuran; hexane / 2 h / -75 °C 1.2: tetrahydrofuran; hexane 2.1: 3.62 g / HCl / H2O / pH 1 View Scheme