Multi-step reaction with 12 steps
1: K2CO3 / ethanol / 10 h / Heating
2: NaOEt / ethanol; tetrahydrofuran / a) -15 deg C, 3 h, b) 4 deg C, 12 h
3: xylene / 3 h / Heating
4: 93 percent / KOH / ethanol / 1.5 h / Heating
5: 73 percent / copper chromite / quinoline / 3 h / 230 °C
6: acetic acid / CH2Cl2 / 2 h / Ambient temperature
7: 1.) iodomethane / 1.) THF, from 0 deg C to 4 deg C, 30 h, 2.) water, 80 deg C, 3.5 h
8: H2, NH3 / Raney nickel / ethanol / 48 h / 2508 Torr / Ambient temperature
9: 1.) NaOEt / 1.) ethanol, 0 deg C, 1 h, 2.) ethanol, RT, 3 h
10: H2 / 10percent Pd/C / ethanol / 48 h / 2508 Torr / Ambient temperature
11: Fremy's salt, aq. KH2PO4 / acetone / 4 h / 0 °C
12: 1.) t-BuOK / 1.) THF, 0 deg C, 1 h, 2.) THF, RT, 3 h
With
potassium hydroxide; potassium dihydrogenphosphate; potassiuim nitrosodisulfonate; copper chromite; potassium tert-butylate; ammonia; hydrogen; sodium ethanolate; potassium carbonate; acetic acid; methyl iodide;
palladium on activated charcoal; nickel;
In
tetrahydrofuran; quinoline; ethanol; dichloromethane; acetone; xylene;
