1: 69 percent / pyridinium dichromate / dimethylformamide / 10 h / 20 °C 2: 93 percent / H2SO4 / 22 h / Heating View Scheme

Multistep reaction;

pyridinium chlorochromate 1.) CH2Cl2, RT, 4 h, 2.) THF, RT, 1 h; Yield given. Multistep reaction;

1.1: 75 percent / CrO3; H2SO4 / acetone 2.1: 98 percent / H2SO4 3.1: O3 / CH2Cl2 / -78 °C 3.2: 72 percent / Zn; HOAc 4.1: 78 percent / CrCl2; NiBr2 / dimethylformamide 5.1: 93 percent / DMP / CH2Cl2 View Scheme

1: 95 percent / Amberlist15 / CH2Cl2 / 6 h / Ambient temperature 2: 1.) O3, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 2.) CH2Cl2, from -78 deg C to RT 3: 1.) n-BuLi / 1.) THF, hexane, RT, 15 min, 2.) THF, hexane, RT, 18 h 4: 91 percent / H2 / 10percent Pd/C / ethanol / 12 h 5: 94 percent / p-toluenesulfonic acid, H2O / tetrahydrofuran / 18 h / Ambient temperature 6: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) CH2Cl2, 0 deg C, 20 min 7: 1.) t-BuOK / 1.) THF, RT, 30 min, 2.) THF, 1 h 8: 91 percent / ethanethiol, NaH / dimethylformamide / 3 h / Heating 9: 62.4 percent / N-bromosuccinimide (NBS) / CCl4 / 4 h / Ambient temperature 10: 31 percent / salcomine, O2 / dimethylformamide / 20 h / Ambient temperature 11: 97 percent / Pd(PPh3)4, 2 N aq. Na2CO3 / tetrahydrofuran / 0.17 h / 90 °C 12: 80 mg / HClO4 / CH2Cl2 / 2 h / Ambient temperature View Scheme

1: picric acid 2: 1) BuLi; 2) H2O / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / 1) r.t., 2 h 3: TsOH / methanol / 0.33 h / Ambient temperature 4: 96 percent / 1) 0.02N H2SO4; 2) 2N KOH / ethyl acetate; dioxane / 1) reflux, 30 min; 2) reflux, 30 min 5: diethyl ether; methanol View Scheme

1: picric acid 2: 1) BuLi; 2) H2O / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / 1) r.t., 2 h 3: TsOH / methanol / 0.33 h / Ambient temperature 4: 96 percent / 1) 0.02N H2SO4; 2) 2N KOH / ethyl acetate; dioxane / 1) reflux, 30 min; 2) reflux, 30 min View Scheme

1: picric acid 2: 1) BuLi; 2) H2O / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / 1) r.t., 2 h 3: TsOH / methanol / 0.33 h / Ambient temperature 4: 96 percent / 1) 0.02N H2SO4; 2) 2N KOH / ethyl acetate; dioxane / 1) reflux, 30 min; 2) reflux, 30 min 5: diethyl ether; methanol 6: 98 percent / quinoline, H2 / 5percent Pd/Lindlar / cyclohexane / 0.75 h 7: 95 percent / 2N KOH / methanol View Scheme

2,4,6-trinitro-phenol

1: 67 percent / DMAP; Et3N / CH2Cl2 / 24 h / 20 °C 2: 98 percent / H2 / Pd/C / ethyl acetate / 24 h / 20 °C / atmospheric pressure View Scheme