triethylamine in N,N-dimethyl-formamide Acylation;

dihydrogen peroxide; Titanium(IV) oxide in methanol T=60°C; 8 h;

N-chloro-succinimide in water T=24.9°C; pH 10.6; ΔH(excit.), ΔS(excit.); KineticsThermodynamic data;

Condensation;

in ethylene glycol dimethyl ether at -15 to 50°C;

NiII chloride hexahydrate in toluene 13 h; Dean-StarkReflux;

1: 86 percent / acetic acid / 0.08 h / Heating 2: 64 percent / HCl (g) / diethyl ether / 10 degC, 3h, then r.t., overnight 3: 83 percent / H2O / 1 h / 80 °C 4: 87 percent / triethylamine / toluene / 6 h / 95 °C / r.t., overnight 5: H2 / PtO2 / ethyl acetate / 3.5 h / Ambient temperature 6: H2 / PtO2 / acetic acid; ethyl acetate / 1.5 h / Ambient temperature 7: 90 percent / triethylamine / tetrahydrofuran / Ambient temperature; overnight 8: 96 percent / H2 / 5percent Pd-on-carbon / acetic acid; ethanol / 1.5 h / 40 °C / 2280 Torr 9: 1M diborane / tetrahydrofuran / 1 h / Heating View Scheme

sodium nitrite in water T=0 - 20°C; 0.416667 h;

in acetic acid 0.0833333 h; Heating;

1: 86 percent / acetic acid / 0.08 h / Heating 2: 64 percent / HCl (g) / diethyl ether / 10 degC, 3h, then r.t., overnight 3: 83 percent / H2O / 1 h / 80 °C View Scheme