1: 1) NaOH; 2) CH3COONa / 1) methanol, water, THF, 10 deg C, 1 h; 2) 140 deg C, 30 min. 2: 85 percent / Fe powder / ethanol; acetic acid / 0.42 h View Scheme

1: 1) NaOH; 2) CH3COONa / 1) methanol, water, THF, 10 deg C, 1 h; 2) 140 deg C, 30 min. 2: 85 percent / Fe powder / ethanol; acetic acid / 0.42 h 3: 99 percent / K2CO3 / methanol / 0.58 h / Ambient temperature View Scheme

1: 1) NaOH; 2) CH3COONa / 1) methanol, water, THF, 10 deg C, 1 h; 2) 140 deg C, 30 min. 2: 90 percent / conc. H2SO4 / methanol / 24 h / Ambient temperature 3: Jones reagent / acetone / 4 h 4: conc. H2SO4 / Ambient temperature; overnight 5: 65 percent / Fe powder / ethanol; acetic acid / 0.42 h 6: 47 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / benzene / 16 h / Ambient temperature View Scheme

1: 1) NaOH; 2) CH3COONa / 1) methanol, water, THF, 10 deg C, 1 h; 2) 140 deg C, 30 min. 2: 90 percent / conc. H2SO4 / methanol / 24 h / Ambient temperature 3: Jones reagent / acetone / 4 h 4: conc. H2SO4 / Ambient temperature; overnight 5: 65 percent / Fe powder / ethanol; acetic acid / 0.42 h 6: 68 percent / Cu2Br2, Na2CO3 / various solvent(s) / 5.5 h / 170 °C 7: 81 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / benzene / 6 h / Heating View Scheme

1: 1) NaOH; 2) CH3COONa / 1) methanol, water, THF, 10 deg C, 1 h; 2) 140 deg C, 30 min. 2: 85 percent / Fe powder / ethanol; acetic acid / 0.42 h 3: 99 percent / K2CO3 / methanol / 0.58 h / Ambient temperature 4: 58 percent / Cu2Br2, Na2CO3 / various solvent(s) / 3 h / 170 °C View Scheme