Multi-step reaction with 10 steps
1: 1.) aluminium chloride, 2.) sodium dithionite, sodium hydroxide / 1.) 1,1,2,2-tetrachloroethane, room temperature, 16 h, steam-bath, 2 h, 2.) methanol, water, room temperature, 21 h, reflux 24 h
2: 77 percent / hydrogen / 10percent palladium-carbon / acetic acid / 4 h / 64 °C
3: H2SO4 / Heating
4: 91 percent / potassium carbonate / acetone / 48 h / Heating
5: 100 percent / lithium aluminium hydride / diethyl ether / 2 h / Heating
6: 88 percent / pyridine / 1.) 0 deg C, 3 h, 2.) -5 deg C, 24 h
7: 89 percent / lithium bromide / acetone / 24 h / Ambient temperature
8: 42 percent / Mg, 3-(4-benzyloxyphenyl)propanal / tetrahydrofuran / 18 h / Ambient temperature
9: 75 percent / pyridinium chlorochromate / CH2Cl2
10: hydrogen / 5percent palladium-carbon / acetic acid
With
pyridine; sodium hydroxide; lithium aluminium tetrahydride; aluminium trichloride; sodium dithionite; sulfuric acid; hydrogen; 3-(4-(benzyloxy)phenyl)propanal; potassium carbonate; magnesium; pyridinium chlorochromate; lithium bromide;
palladium on activated charcoal;
In
tetrahydrofuran; diethyl ether; dichloromethane; acetic acid; acetone;