Multi-step reaction with 22 steps
1: 99 percent / H2 / Raney nickel (W-7) / methanol / 4 h / 130 °C / 95616.1 Torr
2: 8N Jones chromic acid reagent / acetone / 1 h / Ambient temperature
3: p-toluenesulfonic acid monohydrate / benzene / 20 h / Heating; azeotropic removal of water
4: p-toluenesulfonic acid monohydrate, H2O / acetone / 2 h / Heating
5: 86 percent / Na, isopropyl alcohol / toluene / 1 h / Heating
6: 85 percent / 0.5N HCl / tetrahydrofuran / 1 h / Heating
7: 97 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 20 h / Ambient temperature
8: 60 percent NaH (mineraloil) / benzene / 20 h / Ambient temperature
9: 1.)p-toluenesulfonyl chloride, pyridine / 1.) 0 deg C, 3 h, 2.) 0 deg C, 20 h
10: 1.) potassium tert-butoxide / 1.) t-BuOH, room temp., 1 h, 2.) 30 min.
11: 20percent aq. KOH / bis-(2-hydroxy-ethyl) ether / 15 h / Heating
12: acetic anhydride, CH3CO2Na / 1.5 h / Heating
13: diethyl ether / 1.5 h / -25 °C
14: 10percent aq. KOH / methanol / 1.5 h / Heating
15: p-toluenesulfonic acid monohydrate / methanol / 1 h / Ambient temperature
16: pyridinium p-toluenesulfonate / CH2Cl2 / 6 h / Ambient temperature
17: 1.) diisopropylamine, 1.53M n-butyllithium/n-hexane / 1.) THF, -78 deg C, 30 min, 2.) -78 deg C, 20 min
18: 1.) oxalyl chloride, dimethyl sulfoxide, 2.) triethylamine / 1.) CH2Cl2, -70 deg C, 1 h, 2.) -70 deg C to 0 deg C
19: 67 percent / DDQ / diethyl ether / 4 h / Ambient temperature
20: 77 percent / 4.17M tert-butylhydroperoxide/toluene, 40percent Triton B/MeOH / tetrahydrofuran / 1 h / Ambient temperature
21: 1.) 1.53M n-butyllithium/n-hexane, 2.) Wittig reagent / 1.) 1,2-dimethoxyethane, 0 deg C, 2 h, 2.) 0 deg C, 30 min, 1,2-dimethoxyethane; 2 h, r.t.
22: 74 percent / pyridinium p-toluenesulfonate / methanol / 1 h / 45 °C
With
pyridine; hydrogenchloride; methanol; tert.-butylhydroperoxide; potassium hydroxide; n-butyllithium; oxalyl dichloride; hexane; potassium tert-butylate; water; hydrogen; sodium acetate; sodium; pyridinium p-toluenesulfonate; acetic anhydride; chromic acid; N-benzyl-trimethylammonium hydroxide; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; diisopropylamine; p-toluenesulfonyl chloride; methyl (triphenylphosphoranylidene)acetate; isopropyl alcohol; toluene; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
Raney nickel (W-7);
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetone; toluene; diethylene glycol; benzene;