hydrogenchloride in tetrahydrofuran T=20°C; 1 h;

hydrogenchloride in diethyl ether

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

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

1: 79.5 percent / Jones reagent / acetone / 1 h 2: 92.5 percent / sodium methoxide / benzene / 13 h / Ambient temperature 3: 1.) 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, 2.) conc aq. HCl / 1.) benzene, room temperature, 30 min, 2.) 22 h 4: 74 percent / anhydrous potassium carbonate / dimethylformamide / 2.5 h 5: 98 percent / toluene / 0.75 h 6: 49 percent / 10percent aq. HCl / diethyl ether / 25 h View Scheme

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

1: 92.5 percent / sodium methoxide / benzene / 13 h / Ambient temperature 2: 1.) 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, 2.) conc aq. HCl / 1.) benzene, room temperature, 30 min, 2.) 22 h 3: 74 percent / anhydrous potassium carbonate / dimethylformamide / 2.5 h 4: 98 percent / toluene / 0.75 h 5: 49 percent / 10percent aq. HCl / diethyl ether / 25 h View Scheme

1: 74 percent / anhydrous potassium carbonate / dimethylformamide / 2.5 h 2: 98 percent / toluene / 0.75 h 3: 49 percent / 10percent aq. HCl / diethyl ether / 25 h View Scheme

1: 98 percent / toluene / 0.75 h 2: 49 percent / 10percent aq. HCl / diethyl ether / 25 h View Scheme

1: 98 percent / lithium bromide / diethyl ether; tetrahydrofuran / Ambient temperature 2: sodium, liquid ammonia / ethanol 3: 71 percent / 10percent aq. HCl 4: 85 percent / diethyl ether / 0.5 h 5: 1.) sodium borohydride, 2.) 10percent aq. sodium hydroxide / 1.) abs. ethanol, 1 h 6: 64 percent / zinc dust, anhydrous copper(II) chloride / diethyl ether 7: 79.5 percent / Jones reagent / acetone / 1 h 8: 92.5 percent / sodium methoxide / benzene / 13 h / Ambient temperature 9: 1.) 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, 2.) conc aq. HCl / 1.) benzene, room temperature, 30 min, 2.) 22 h 10: 74 percent / anhydrous potassium carbonate / dimethylformamide / 2.5 h 11: 98 percent / toluene / 0.75 h 12: 49 percent / 10percent aq. HCl / diethyl ether / 25 h View Scheme