sodium methylate in tetrahydrofuran; methanol T=20°C; 6 h;

1: With sodium hydride in tetrahydrofuran; toluene; benzene 4 h; Reflux; 2: With water; potassium hydroxide in tetrahydrofuran; toluene; benzene 1 h; Reflux; 3: With hydrogenchloride in tetrahydrofuran; water; toluene; benzene pH=1;

1: acetic anhydride / 1,3,5-trimethyl-benzene / 1 h / 100 °C / 150.01 Torr 2: pyridine / dichloromethane / 0 - 20 °C 3: tetrahydrofuran; diethyl ether / 2 h / -75 °C 4: hydrogenchloride / water; 1,3,5-trimethyl-benzene / 1 h / |Reflux 5: sodium methylate / tetrahydrofuran; methanol / 6 h / 20 °C View Scheme

1: pyridine / dichloromethane / 0 - 20 °C 2: tetrahydrofuran; diethyl ether / 2 h / -75 °C 3: hydrogenchloride / water; 1,3,5-trimethyl-benzene / 1 h / |Reflux 4: sodium methylate / tetrahydrofuran; methanol / 6 h / 20 °C View Scheme

1: potassium hydroxide / water / 7.5 h / |Reflux 2: acetic anhydride / 1,3,5-trimethyl-benzene / 1 h / 100 °C / 150.01 Torr 3: pyridine / dichloromethane / 0 - 20 °C 4: tetrahydrofuran; diethyl ether / 2 h / -75 °C 5: hydrogenchloride / water; 1,3,5-trimethyl-benzene / 1 h / |Reflux 6: sodium methylate / tetrahydrofuran; methanol / 6 h / 20 °C View Scheme

1: N,N-dimethyl-formamide; thionyl chloride / toluene / 40 - 70 °C 2: iron tribromide / toluene; tetrahydrofuran / -50 °C 3: sodium methylate / tetrahydrofuran; methanol / 6 h / 20 °C View Scheme

1: iron tribromide / toluene; tetrahydrofuran / -50 °C 2: sodium methylate / tetrahydrofuran; methanol / 6 h / 20 °C View Scheme

1: hydrogenchloride / water; 1,3,5-trimethyl-benzene / 1 h / |Reflux 2: sodium methylate / tetrahydrofuran; methanol / 6 h / 20 °C View Scheme

1: tetrahydrofuran; diethyl ether / 2 h / -75 °C 2: hydrogenchloride / water; 1,3,5-trimethyl-benzene / 1 h / |Reflux 3: sodium methylate / tetrahydrofuran; methanol / 6 h / 20 °C View Scheme