1: 4-(1-methylethyl)-2-hydroxy-1-methyl benzene With triethylamine; magnesium chloride in acetonitrile 0.25 h; 2: formaldehyd 3.5 h; Heating;

sodium hydroxide; chloroform in water 1) 1h, <60 deg C, 2) 15 min, reflux;

AlCl3, aluminium chloride; sodium iodide in dichloromethane; acetonitrile T=0 - 20°C; 1 h;

K5IO6; sulfuric acid in ethanol 1.) 0 deg C, 2 h, 2.) 0 deg C to room temperature;

1: LiAlH4 / diethyl ether / 0.17 h / Heating 2: 5.2 g / K5IO6, aq. H2SO4 / ethanol / 1.) 0 deg C, 2 h, 2.) 0 deg C to room temperature View Scheme

1: n-butyllithium; N,N,N',N,-tetramethylethylenediamine / diethyl ether / 6 h / 0 - 20 °C 2: sodium iodide; AlCl3, aluminium chloride / acetonitrile; dichloromethane / 1 h / 0 - 20 °C View Scheme

sodium hydroxide; water T=50 - 60°C; Wird vom Nebenprodukt durch Destillation mit Wasserdampf getrennt;

N,N,N',N',N'',N''-hexamethylphosphoric triamide; ethylmagnesium bromide 1.) Et2O, 2.) C6H6, reflux, 3 h; Yield given. Multistep reaction. Yields of byproduct given;

T=170°C; anschliessendes Kochen mit wss. H2SO4;

1.1: acetic acid; bromine / 20.25 h / 20 °C / |Cooling with ice 2.1: potassium carbonate / acetone / 15 h / 30 °C 3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C 3.2: 2 h / |Reflux 4.1: potassium carbonate / acetone / 12 h / 20 °C 5.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / |Inert atmosphere 5.2: 10 h / -78 - -30 °C / |Inert atmosphere 6.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C 7.1: acetic anhydride; sodium acetate / 2 h / |Reflux 8.1: sodium hydroxide / methanol; water / |Reflux 9.1: potassium carbonate / acetone / 12 h / 20 °C 10.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C 10.2: 10 h / 20 °C 11.1: silver(l) oxide / methanol / 3 h / 20 °C 12.1: potassium carbonate / acetone / 5 h / 20 °C 13.1: dichloromethane / 0.5 h / 20 °C 14.1: lithium hydroxide hydrate / water; tetrahydrofuran / 1 h / 20 °C 15.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 16.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / |Inert atmosphere 17.1: MeC(O)OOBu-t / 1,2-dichloro-ethane / 4 h / 80 °C / |Inert atmosphere View Scheme