hydrogen fluoride 15 h; Ambient temperature;

1: 83 percent / zinc dust, iodine / benzene; diethyl ether / 1.) 15 min, reflux, 2.) 2h, reflux 2: 1.) p-TsOH, 2.) 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) / 1.) benzene, reflux, 2h, 2.) reflux, 4h 3: 88 percent / aq. KOH / methanol / 1 h / Heating 4: 88 percent / anhydrous HF / 15 h / Ambient temperature View Scheme

1: 70 percent / polyphosphoric acid / 3 h / 80 °C 2: 83 percent / zinc dust, iodine / benzene; diethyl ether / 1.) 15 min, reflux, 2.) 2h, reflux 3: 1.) p-TsOH, 2.) 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) / 1.) benzene, reflux, 2h, 2.) reflux, 4h 4: 88 percent / aq. KOH / methanol / 1 h / Heating 5: 88 percent / anhydrous HF / 15 h / Ambient temperature View Scheme

1: 88 percent / aq. KOH / methanol / 1 h / Heating 2: 88 percent / anhydrous HF / 15 h / Ambient temperature View Scheme

1: 1.) p-TsOH, 2.) 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) / 1.) benzene, reflux, 2h, 2.) reflux, 4h 2: 88 percent / aq. KOH / methanol / 1 h / Heating 3: 88 percent / anhydrous HF / 15 h / Ambient temperature View Scheme

Erwaermen des Saeurechlorids mit Aluminiumchlorid in Schwefelkohlenstoff;

2: LiAlH4, AlCl3 View Scheme

(i), (ii) (reduction); Multistep reaction;

2: LiAlH4, AlCl3 View Scheme

(i), (ii) (reduction); Multistep reaction;