im Rohr;

diethyl ether

potassium hydroxide

1: 1.) NaH, 2.) CuBr / 1.) DMF, 2.) DMF, from 75 deg C to 80 deg C, 2.5 h 2: 1.) aq. dithionite, 2.) concd. H2SO4 / 1.) CH2Cl2, 5 min, 2.) 60 deg C, 20 min 3: 68 percent / 30percent aq. H2O2, TFA / CHCl3 / 5 h / 0 °C View Scheme

man verseift den entstehenden Ester mit KOH;

1.1: 17 percent / FeCl3/SiO2 / 20 h / 60 °C 2.1: n-BuLi / hexane; tetrahydrofuran / 0.75 h / -78 °C 2.2: 75 percent / hexane; tetrahydrofuran / 1.5 h / -78 - 20 °C 3.1: 67 percent / aq. HCl / methanol / 13 h / Heating 4.1: NaH / hexamethylphosphoric acid triamide 4.2: 59 percent / hexamethylphosphoric acid triamide / 2 h / 20 °C View Scheme

1: methyl 2-hydroxy-4-methoxy-6-methylbenzoate With dihydrogen peroxide; iodine in ethanol 2: dimethyl sulfate With potassium carbonate in acetone T=56°C; 24 h; Further stages.;

1: methyl 2-hydroxy-4-methoxy-6-methylbenzoate With dihydrogen peroxide; iodine in ethanol 2: dimethyl sulfate With potassium carbonate in acetone T=56°C; 24 h; Further stages.;

1: 73 percent / TiCl4 / CH2Cl2 / 5.5 h / Ambient temperature 2: 94 percent / 15percent KOH / 2 h / Heating 3: 86 percent / 2,2'-bipyridine, CuO2 / bis-(2-methoxy-ethyl) ether / 5 h / Heating View Scheme