1: aluminium chloride; nitrobenzene 2: amalgamated zinc; aqueous hydrochloric acid; acetic acid 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 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: 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 6: 95 percent / Sodium borohydride / dimethylformamide / 6 h / Ambient temperature 7: 62 percent / p-TsOH / benzene / 0.75 h / Heating View Scheme

PPA T=80°C; 3 h;

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