methanesulfonic acid T=90 - 95°C; 1 h; Yield given. Yields of byproduct given;

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1: 84 percent / zink dust, iodine / benzene; diethyl ether / 2 h / Heating 2: 1.) p-TsOH, 2.) 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) / 1.) benzene, reflux, 2h, 2.) reflux, 6h 3: 91 percent / KOH / H2O; methanol / 1 h / Heating 4: 84 percent / anhydrous HF / 15 h / Ambient temperature 5: NaBH4 / tetrahydrofuran; methanol 6: Al2O3 / benzene / 0.75 h / Heating View Scheme

1: diethyl ether; benzene 2: palladium coal / 300 - 310 °C / Erhitzen unter Stickstoff 3: Na2Cr2O7; propionic acid View Scheme

1: diethyl ether / 0 °C 2: p-toluenesulfonic acid / benzene / 0.25 h / 50 °C 3: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / benzene / 3 h / Heating View Scheme