dihydrogen peroxide; AcrH(+)ClO4(-) in water; acetonitrile T=20°C; Baeyer-Villiger oxidation; 20 h; UV-irradiation;

hydrogen; palladium on activated charcoal in ethanol P=2327.17 - 2585.74 Torr;

1: 92.7 percent / H2 / Pd/C / ethanol / 2585.74 Torr 2: 51 percent / POCl3 / 0 - 40 °C 3: 86.2 percent / NaBH4 / methanol / 0 - 5 °C 4: 85.6 percent / H2 / Pd/C / ethanol / 2327.17 - 2585.74 Torr View Scheme

1: 77 percent / AlCl3 / nitrobenzene / 3 h / Heating 2: 99 percent / diethyl ether 3: 92.7 percent / H2 / Pd/C / ethanol / 2585.74 Torr 4: 51 percent / POCl3 / 0 - 40 °C 5: 86.2 percent / NaBH4 / methanol / 0 - 5 °C 6: 85.6 percent / H2 / Pd/C / ethanol / 2327.17 - 2585.74 Torr View Scheme

1: 99 percent / diethyl ether 2: 92.7 percent / H2 / Pd/C / ethanol / 2585.74 Torr 3: 51 percent / POCl3 / 0 - 40 °C 4: 86.2 percent / NaBH4 / methanol / 0 - 5 °C 5: 85.6 percent / H2 / Pd/C / ethanol / 2327.17 - 2585.74 Torr View Scheme

1: 84 percent / air, CuCl / PdCl2 2: H(1+) / methanol 3: 1.) m-CPBA, 2.) acid View Scheme

1: MeONa / Ambient temperature 2: CF3COOH / 0.02 h / Ambient temperature 3: 84 percent / air, CuCl / PdCl2 4: H(1+) / methanol 5: 1.) m-CPBA, 2.) acid View Scheme

1: 96 percent / 2,6-di-tert-butyl-p-cresole, Lipase PS / diisopropyl ether; H2O / 1.5 h / Ambient temperature 2: 91 percent / 4-dimethylaminopyridine, pyridine / CH2Cl2 / 15 h / Ambient temperature 3: 93 percent / guanidine / ethanol / 1 h / Ambient temperature 4: 99 percent / pyridine / CH2Cl2 / 40 h / Ambient temperature 5: 88 percent / dimethylsulfoxide / 24 h / 90 °C 6: 1.) aq. 2M-NaOH; 2.) aq. 2M-NaOH / 1.) ETOH, r.t., 18 h; 2.) 3h reflux View Scheme

1: 74 percent / 1.) sodium hydride / 1.) mineral oil, THF, r.t., 30 min; 2.) THF, 4 h, reflux 2: 95 percent / LiAlH4 / tetrahydrofuran / 4 h / Heating 3: 96 percent / 2,6-di-tert-butyl-p-cresole, Lipase PS / diisopropyl ether; H2O / 1.5 h / Ambient temperature 4: 91 percent / 4-dimethylaminopyridine, pyridine / CH2Cl2 / 15 h / Ambient temperature 5: 93 percent / guanidine / ethanol / 1 h / Ambient temperature 6: 99 percent / pyridine / CH2Cl2 / 40 h / Ambient temperature 7: 88 percent / dimethylsulfoxide / 24 h / 90 °C 8: 1.) aq. 2M-NaOH; 2.) aq. 2M-NaOH / 1.) ETOH, r.t., 18 h; 2.) 3h reflux View Scheme

1: 95 percent / LiAlH4 / tetrahydrofuran / 4 h / Heating 2: 96 percent / 2,6-di-tert-butyl-p-cresole, Lipase PS / diisopropyl ether; H2O / 1.5 h / Ambient temperature 3: 91 percent / 4-dimethylaminopyridine, pyridine / CH2Cl2 / 15 h / Ambient temperature 4: 93 percent / guanidine / ethanol / 1 h / Ambient temperature 5: 99 percent / pyridine / CH2Cl2 / 40 h / Ambient temperature 6: 88 percent / dimethylsulfoxide / 24 h / 90 °C 7: 1.) aq. 2M-NaOH; 2.) aq. 2M-NaOH / 1.) ETOH, r.t., 18 h; 2.) 3h reflux View Scheme