T=200°C; im Autoklaven; d-pulegone;

T=70°C; Hydrogenation;

Hydrogenation; d-pulegone;

iron(III) oxide T=380 - 400°C; im Hochdruckautoklaven;

T=175 - 220°C; Reaktion in der Dampfphase (300grad);

1: 75 percent / "70percent" calcium hypochlorite / H2O; CH2Cl2 2: 84 percent / aluminum chloride / CH2Cl2 / 4 h / 0 °C View Scheme

1.1: sodium hydrogencarbonate; bromine / diethyl ether / 0.5 h / Inert atmosphere; Cooling with ice 2.1: diethyl ether / 20 °C / Cooling with ice 2.3: 2.5 h / Reflux 3.1: ozone / ethyl acetate / 3.5 h / -68 °C 3.2: 0.5 h 4.1: ammonium acetate / methanol / 20 h / 20 °C / Inert atmosphere 5.1: 17 h / 150 °C 6.1: trichlorophosphate / 0.08 h / Reflux 7.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 48 h / 20 °C 8.1: 2 h / 110 °C 9.1: 1-methyl-pyrrolidin-2-one / 12 h / 110 °C 10.1: water; lithium hydroxide hydrate / tetrahydrofuran / 4.5 h / 0 - 20 °C 10.2: 0.08 h / 0 °C 11.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C 11.2: 0.5 h / -78 - 20 °C 12.1: triethylamine; formic acid / Ru catalyst / dichloromethane / 18 h / Inert atmosphere View Scheme

1: 49 percent / p-Toluenesulfonic acid, 4A molecular sieves / toluene / 240 h / Heating 2: benzene / 60 h / Heating 3: 1.5 percent / Hydroxylamine hydrochloride, hydrochloric acid / ethanol; H2O / 4 h / Heating View Scheme

1: 94 percent / 30percent H2O2; LiOH / methanol / 8 h / 25 °C 2: 84 percent / tetrahydrofuran / 18 h / Heating 3: 90 percent / mCPBA / CH2Cl2 / 2 h / -30 °C View Scheme

boron trifluoride diethyl etherate; sodium cyanoborohydride in tetrahydrofuran 12 h; Ambient temperature; Yield given. Yields of byproduct given;