Multi-step reaction with 8 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, room temperature, 21 h, reflux, 24 h
2: 88 percent / hydrogen / palladium-carbon / acetic acid / 1.5 h / Ambient temperature
3: 59 percent / lithium aluminium hydride / diethyl ether
4: 62 percent / pyridine
5: 80 percent / lithium bromide / acetone / 24 h / Ambient temperature
6: magnesium (from magnesium chloride and potassium metal, 3-(4-methoxyphenyl)propanal / tetrahydrofuran
7: 74 percent / pyridinium chlorochromate / CH2Cl2 / 4.5 h
8: 54 percent / hydrogen chloride / CH2Cl2 / 0.5 h / -25 °C
With
pyridine; hydrogenchloride; sodium hydroxide; lithium aluminium tetrahydride; aluminium trichloride; sodium dithionite; 3-(4-methoxyphenyl)propional; hydrogen; magnesium; pyridinium chlorochromate; lithium bromide;
palladium on activated charcoal;
In
tetrahydrofuran; diethyl ether; dichloromethane; acetic acid; acetone;