1: 4-(1-methylethyl)-2-hydroxy-1-methyl benzene With sodium hydroxide; Amberlite IRA 400 2: ethyl halide in acetone 0.583333 h; Further stages.;

T=400 - 500°C;

1: With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in tetrahydrofuran T=20°C; Diels-Alder reaction; 24 h; 2: With trifluoroacetic acid 12 h; Further stages.;

1: With 2-iodoxybenzoic acid in tetrahydrofuran T=20°C; 24 h; 2: With trifluoroacetic acid in tetrahydrofuran 12 h; Further stages.;

1: With 2-iodoxybenzoic acid in tetrahydrofuran T=20°C; 24 h; 2: With trifluoroacetic acid in tetrahydrofuran 12 h; Further stages.;

sulfuryl dichloride

pyridine in dichloromethane T=0 - 20°C; 1 h; Inert atmosphere;

1.1: tin(IV) chloride; triethylamine / toluene / 0.33 h / 20 °C / |Inert atmosphere 1.2: 8 h / 100 °C / |Inert atmosphere 2.1: acetic acid; bromine / 20.25 h / 20 °C / |Cooling with ice 3.1: potassium carbonate / acetone / 15 h / 30 °C 4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C 4.2: 2 h / |Reflux 5.1: potassium carbonate / acetone / 12 h / 20 °C 6.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / |Inert atmosphere 6.2: 10 h / -78 - -30 °C / |Inert atmosphere 7.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C 8.1: acetic anhydride; sodium acetate / 2 h / |Reflux 9.1: sodium hydroxide / methanol; water / |Reflux 10.1: potassium carbonate / acetone / 12 h / 20 °C 11.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C 11.2: 10 h / 20 °C 12.1: silver(l) oxide / methanol / 3 h / 20 °C 13.1: potassium carbonate / acetone / 5 h / 20 °C 14.1: dichloromethane / 0.5 h / 20 °C 15.1: lithium hydroxide hydrate / water; tetrahydrofuran / 1 h / 20 °C 16.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 17.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / |Inert atmosphere View Scheme

sulfuric acid; sodium nitrite

1: 4-(1-methylethyl)-2-hydroxy-1-methyl benzene With sodium hydroxide in tetrahydrofuran T=50°C; 1 h; Inert atmosphere; 2: methyl iodide in tetrahydrofuran T=50°C; Inert atmosphere;