1: sodium, liquid ammonia / ethanol 2: 71 percent / 10percent aq. HCl View Scheme

1: sodium, liquid ammonia / ethanol 2: 71 percent / 10percent aq. HCl 3: 85 percent / diethyl ether / 0.5 h 4: 1.) sodium borohydride, 2.) 10percent aq. sodium hydroxide / 1.) abs. ethanol, 1 h 5: 64 percent / zinc dust, anhydrous copper(II) chloride / diethyl ether 6: 79.5 percent / Jones reagent / acetone / 1 h 7: 92.5 percent / sodium methoxide / benzene / 13 h / Ambient temperature 8: 1.) 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, 2.) conc aq. HCl / 1.) benzene, room temperature, 30 min, 2.) 22 h 9: 74 percent / anhydrous potassium carbonate / dimethylformamide / 2.5 h 10: 98 percent / toluene / 0.75 h 11: 49 percent / 10percent aq. HCl / diethyl ether / 25 h View Scheme