lithium aluminium tetrahydride; diethyl ether; benzene

1: 2,5-dimethoxy-benzyl alcohol With n-butyllithium in tetrahydrofuran 3 h; Reflux; 2: carbon dioxide in tetrahydrofuran T=-78 - 20°C; 1 h; 3: With hydrogenchloride in tetrahydrofuran; water T=20°C; 3 h; regioselective reaction;

hydrogen; palladium on activated charcoal in methanol P=2585.81 Torr; 6 h;

potassium carbonate in acetone 24 h; Heating;

oxygen in toluene Heating;

1: 72 percent / cc. nitric acid / 3 h / 0 - 2 °C 2: 93 percent / H2 / 10 percent Pd-C / ethanol / 6 h / 38000 Torr 3: 1.) cc. hydrochloric acid, 97 percent isoamyl nitrite; 2.) propylene oxide / 1.) abs. ethanol, 0 deg C, 10 min; 2.) 1,2-dichloroethane, reflux 4: 78 percent / Amberlyst 15 ion exchange resin / methanol / Ambient temperature 5: 36 percent / air / toluene / 96 h / Heating View Scheme

1: 93 percent / H2 / 10 percent Pd-C / ethanol / 6 h / 38000 Torr 2: 1.) cc. hydrochloric acid, 97 percent isoamyl nitrite; 2.) propylene oxide / 1.) abs. ethanol, 0 deg C, 10 min; 2.) 1,2-dichloroethane, reflux 3: 78 percent / Amberlyst 15 ion exchange resin / methanol / Ambient temperature 4: 36 percent / air / toluene / 96 h / Heating View Scheme

1: 85 percent / potassium permanganate / H2O / 1 h / 80 °C 2: 72 percent / cc. nitric acid / 3 h / 0 - 2 °C 3: 93 percent / H2 / 10 percent Pd-C / ethanol / 6 h / 38000 Torr 4: 1.) cc. hydrochloric acid, 97 percent isoamyl nitrite; 2.) propylene oxide / 1.) abs. ethanol, 0 deg C, 10 min; 2.) 1,2-dichloroethane, reflux 5: 78 percent / Amberlyst 15 ion exchange resin / methanol / Ambient temperature 6: 36 percent / air / toluene / 96 h / Heating View Scheme

Wilkinson's catalyst T=100°C; 5 h;

magnesium oxide; trifluoroacetic acid; lithium chloride; palladium dichloride; Tl(OCOCF3)3 1.) THF, 25 deg C, 16 h, 2.) MeOH, room temperature, overnight; Yield given. Multistep reaction;