1: 84 percent / acetic acid, ammonium acetate / benzene / 6 h / Heating 2: 95 percent / H2 / 5percent Pd/C / aq. ethanol / 2 h / 760 Torr / Ambient temperature 3: 92 percent / KOH / ethane-1,2-diol; H2O / Heating 4: 95 percent / polyphosphoric acid / 1.) 95-100 deg C; 2.) 105-115 deg C, 2 h; 3.) rt, 8 h 5: 1.) NaH / 1.) benzene, 62-64 deg C, 2 h; 2.) benzene, 70 deg C, 3 h 6: 1.) NaBH4 / 1.) methanol, 0 deg C, 30-45 min; 2.) methanol, r.t., 3-4 h 7: 79 percent / p-toluenesulfonic acid monohydrate, hydroquinone / benzene / Heating View Scheme

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

1: 95 percent / H2 / 5percent Pd/C / aq. ethanol / 2 h / 760 Torr / Ambient temperature 2: 92 percent / KOH / ethane-1,2-diol; H2O / Heating 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

1: 95 percent / polyphosphoric acid / 1.) 95-100 deg C; 2.) 105-115 deg C, 2 h; 3.) rt, 8 h 2: 1.) NaH / 1.) benzene, 62-64 deg C, 2 h; 2.) benzene, 70 deg C, 3 h 3: 1.) NaBH4 / 1.) methanol, 0 deg C, 30-45 min; 2.) methanol, r.t., 3-4 h 4: 79 percent / p-toluenesulfonic acid monohydrate, hydroquinone / benzene / Heating View Scheme

1: 1.) NaH / 1.) benzene, 62-64 deg C, 2 h; 2.) benzene, 70 deg C, 3 h 2: 1.) NaBH4 / 1.) methanol, 0 deg C, 30-45 min; 2.) methanol, r.t., 3-4 h 3: 79 percent / p-toluenesulfonic acid monohydrate, hydroquinone / benzene / Heating View Scheme

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

1: 92 percent / KOH / ethane-1,2-diol; H2O / Heating 2: 95 percent / polyphosphoric acid / 1.) 95-100 deg C; 2.) 105-115 deg C, 2 h; 3.) rt, 8 h 3: 1.) NaH / 1.) benzene, 62-64 deg C, 2 h; 2.) benzene, 70 deg C, 3 h 4: 1.) NaBH4 / 1.) methanol, 0 deg C, 30-45 min; 2.) methanol, r.t., 3-4 h 5: 79 percent / p-toluenesulfonic acid monohydrate, hydroquinone / benzene / Heating View Scheme

1: 1.) NaBH4 / 1.) methanol, 0 deg C, 30-45 min; 2.) methanol, r.t., 3-4 h 2: 79 percent / p-toluenesulfonic acid monohydrate, hydroquinone / benzene / Heating View Scheme