1.1: 76 percent / Na; EtOH / Heating 2.1: 39.0 g / sodium methoxide / methanol / 2 h / Heating 3.1: LDA / tetrahydrofuran; hexane / 1 h / 0 °C 3.2: 80 percent / tetrahydrofuran; hexane / 1 h / 20 °C 4.1: 43 percent / p-toluenesulfonic acid monohydrate; triethyl orthoformate / CH2Cl2 / 19 h / 25 °C 5.1: 77 percent / potassium bis(trimethylsilyl)amide / diethyl ether; toluene / 2 h / 20 °C 6.1: 80 percent / aq. AcOH / 4 h / Heating 7.1: 97 percent / L-selectride / tetrahydrofuran / 17 h / 0 °C 8.1: diphenylphosphoryl azide; diethyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 17 h / 20 °C 9.1: LiAlH4 / ethanol; diethyl ether / 2 h / 20 °C 10.1: 528 mg / Et3N; DMAP / CH2Cl2 / 17 h / 20 °C 11.1: 83 percent / sodium hydroxide; tetrabutylammonium bromide / toluene; H2O / 0.67 h / 100 °C 12.1: 85 percent / O3; triphenylphosphine / CH2Cl2 / 9 h / -78 - 20 °C 13.1: 92 percent / potassium carbonate; tetrabutylammonium bromide / toluene / 2 h / Heating 14.1: 92 percent / sodium borohydride / ethanol / 1 h / 0 °C 15.1: 70 percent / boron tribromide / CH2Cl2 / 1 h / -40 °C 16.1: Red-Al / toluene / 0.5 h / Heating 17.1: 77 mg / Et3N / CH2Cl2 / 1 h / 25 °C 18.1: 75 percent / hydrogen peroxide / [(C8H17)3NCH3]+3[PO4[W(O)(O2)2]4]3- / 1,2-dichloro-ethane; H2O / 2 h / Heating 19.1: 75 percent / sodium borohydride / ethanol / 2 h / Heating 20.1: sodium periodate; aq. NaHCO3 / tetrahydrofuran / 0.5 h / 25 °C 21.1: 3.9 mg / aq. NaHCO3 / benzene / 0.75 h / Heating 22.1: MnO2 / CH2Cl2 / 0.25 h / 25 °C 22.2: 75 percent / LiAlH4 / tetrahydrofuran / 0.25 h / Heating 23.1: 86 percent / boron tribromide / CHCl3; CH2Cl2 / 0.25 h / 25 °C View Scheme

1.1: 76 percent / Na; EtOH / Heating 2.1: 39.0 g / sodium methoxide / methanol / 2 h / Heating 3.1: LDA / tetrahydrofuran; hexane / 1 h / 0 °C 3.2: 80 percent / tetrahydrofuran; hexane / 1 h / 20 °C 4.1: 43 percent / p-toluenesulfonic acid monohydrate; triethyl orthoformate / CH2Cl2 / 19 h / 25 °C 5.1: 77 percent / potassium bis(trimethylsilyl)amide / diethyl ether; toluene / 2 h / 20 °C 6.1: 80 percent / aq. AcOH / 4 h / Heating 7.1: 97 percent / L-selectride / tetrahydrofuran / 17 h / 0 °C 8.1: diphenylphosphoryl azide; diethyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 17 h / 20 °C 9.1: LiAlH4 / ethanol; diethyl ether / 2 h / 20 °C 10.1: 528 mg / Et3N; DMAP / CH2Cl2 / 17 h / 20 °C 11.1: 83 percent / sodium hydroxide; tetrabutylammonium bromide / toluene; H2O / 0.67 h / 100 °C 12.1: 85 percent / O3; triphenylphosphine / CH2Cl2 / 9 h / -78 - 20 °C 13.1: 92 percent / potassium carbonate; tetrabutylammonium bromide / toluene / 2 h / Heating 14.1: 92 percent / sodium borohydride / ethanol / 1 h / 0 °C 15.1: 70 percent / boron tribromide / CH2Cl2 / 1 h / -40 °C 16.1: Red-Al / toluene / 0.5 h / Heating 17.1: 77 mg / Et3N / CH2Cl2 / 1 h / 25 °C 18.1: 75 percent / hydrogen peroxide / [(C8H17)3NCH3]+3[PO4[W(O)(O2)2]4]3- / 1,2-dichloro-ethane; H2O / 2 h / Heating 19.1: 75 percent / sodium borohydride / ethanol / 2 h / Heating 20.1: sodium periodate; aq. NaHCO3 / tetrahydrofuran / 0.5 h / 25 °C 21.1: 3.9 mg / aq. NaHCO3 / benzene / 0.75 h / Heating 22.1: MnO2 / CH2Cl2 / 0.25 h / 25 °C 22.2: 75 percent / LiAlH4 / tetrahydrofuran / 0.25 h / Heating View Scheme

2,4,6-trimethyl-pyridine; copper(l) iodide in methanol Ullman coupling; 19 h; Heating;

1: K2CO3 / dimethylformamide / 3 h / 20 °C 2: 89 percent / 2,4,6-collidine; copper(I)iodide / methanol / 19 h / Heating View Scheme

sodium hydroxide

acid

1: 14 percent / KOH / 0.8 h / 20 °C / Heating; electrolysis 2: acid View Scheme

potassium hydroxide; oxalic acid 1.) electrolysis, 30 deg C, 3.5 h, 2.) THF, 1.5 h; Yield given. Multistep reaction. Yields of byproduct given;

potassium carbonate; acetone

(i) aq. Na2S2O4, (ii) /BRN= 635994/, K2CO3; Multistep reaction;