1: H2 / 5percent Pd/C / aq. ethanol / 13 h / 760 Torr / Ambient temperature 2: 1.) acetic acid, cc. H2SO4; 2.) acetic acid, cc. H2SO4 / H2O / 1.) 20 h, reflux; 2.) 6 h, reflux 3: 95 percent / polyphosphoric acid / 1.) 95-100 deg C; 2.) 105-115 deg C, 2 h; 3.) rt, 8 h View Scheme

ammonium acetate; acetic acid; benzene

1: H2 / 5percent Pd/C / aq. ethanol / 13 h / 760 Torr / Ambient temperature 2: 1.) acetic acid, cc. H2SO4; 2.) acetic acid, cc. H2SO4 / H2O / 1.) 20 h, reflux; 2.) 6 h, reflux 3: 95 percent / polyphosphoric acid / 1.) 95-100 deg C; 2.) 105-115 deg C, 2 h; 3.) rt, 8 h 4: 1.) NaH / 1.) benzene, 62-64 deg C, 2 h; 2.) benzene, 70 deg C, 3 h 5: 1.) NaBH4 / 1.) methanol, 0 deg C, 30-45 min; 2.) methanol, r.t., 3-4 h 6: 79 percent / p-toluenesulfonic acid monohydrate, hydroquinone / benzene / Heating View Scheme

sulfur in ethanol T=50°C;

2: KOH; ethylene glycol View Scheme

glycerol T=250°C;

T=240 - 250°C;