toluene-4-sulfonic acid; magnesium; dilithium tetrachlorocuprate 1.) 2 h, ether, room t.; 2.) methanol, water, 1 h, reflux; Yield given. Multistep reaction;

1.1: NaOEt / ethanol / 0.12 h / Heating 1.2: ethanol / 1 h / Heating 2.1: KOH / ethanol / 4 h / Heating 3.1: 3 h / 190 °C View Scheme

2: KOH / ethanol; H2O / 5 h / Heating 3: 76 percent / N2H4*H2O, KOH / bis-(2-hydroxy-ethyl) ether; methanol / 125 deg C, 6 h; 195 deg C, 3 h View Scheme

dimethyl sulfoxide Kornblum oxidation; 0.0486111 h; Microwave irradiation;

1: 1.) Mg; 2.) p-TsOH / 1.) Li2CuCl4 / 1.) 2 h, ether, room t.; 2.) methanol, water, 1 h, reflux 2: 89 percent / 48percent HBr / 3 h / Heating 3: 55 percent / potassium tert-butoxide / benzene; dimethylsulfoxide / 0.17 h / 60 - 70 °C View Scheme

1.1: NaOEt / ethanol / 0.12 h / Heating 1.2: ethanol / 1 h / Heating 2.1: KOH / ethanol / 4 h / Heating 3.1: 3 h / 190 °C 4.1: 2.00 g / LiAlH4 / diethyl ether / 20 °C 5.1: red phosphorus; bromine / 0 - 20 °C 6.1: NaOEt / ethanol / 0.12 h / Heating 6.2: ethanol / 1 h / Heating 7.1: KOH / ethanol / 4 h / Heating 8.1: 1.1 g / 3 h / 190 °C View Scheme