Technology Process of (2E,4E,6E,8E)-9-(6-Hydroxymethyl-2,6-dimethyl-3-oxo-cyclohex-1-enyl)-3,7-dimethyl-nona-2,4,6,8-tetraenal
There total 12 articles about (2E,4E,6E,8E)-9-(6-Hydroxymethyl-2,6-dimethyl-3-oxo-cyclohex-1-enyl)-3,7-dimethyl-nona-2,4,6,8-tetraenal which
guide to synthetic route it.
The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:
synthetic route:
- Guidance literature:
-
Multi-step reaction with 11 steps
1: 1.) a) NaH, b) n-BuLi / 1.) a) THF, 0 deg C, 1.5 h, b) hexane, 0 deg C, 1.25 h, 2.) -70 deg C, 1 h
2: 54 percent / methanesulfonic acid / acetic acid / 5.5 h / Ambient temperature
3: 1.) sodium methoxide / 2.) room temp., 16 h
4: 83 percent / sodium borohydride / methanol / 3 h / Ambient temperature
5: p-toluenesulfonic acid / tetrahydrofuran / 1 h / Ambient temperature
6: 68 percent / diisobutylaluminium hydride / tetrahydrofuran; hexane / 2 h / -20 - 0 °C
7: pyridine / 1 h / Ambient temperature
8: 72 percent / aq. H2SO4 / acetone / 1.5 h / Ambient temperature
9: 70 percent / manganese dioxide / CH2Cl2 / 5 h / Ambient temperature
10: 69 percent / sodium hydroxide / methanol; H2O / 0.5 h / Ambient temperature
11: 6.56 g / manganese dioxide / CH2Cl2 / 2 h / Ambient temperature
With
manganese(IV) oxide; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; methanesulfonic acid; sulfuric acid; sodium methylate; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid;
In
tetrahydrofuran; pyridine; methanol; hexane; dichloromethane; water; acetic acid; acetone;
DOI:10.1021/jo00348a042
- Guidance literature:
-
Multi-step reaction with 11 steps
1: 1.) a) NaH, b) n-BuLi / 1.) a) THF, 0 deg C, 1.5 h, b) hexane, 0 deg C, 1.25 h, 2.) -70 deg C, 1 h
2: 54 percent / methanesulfonic acid / acetic acid / 5.5 h / Ambient temperature
3: 1.) sodium methoxide / 2.) room temp., 16 h
4: 83 percent / sodium borohydride / methanol / 3 h / Ambient temperature
5: p-toluenesulfonic acid / tetrahydrofuran / 1 h / Ambient temperature
6: 68 percent / diisobutylaluminium hydride / tetrahydrofuran; hexane / 2 h / -20 - 0 °C
7: pyridine / 1 h / Ambient temperature
8: 72 percent / aq. H2SO4 / acetone / 1.5 h / Ambient temperature
9: 70 percent / manganese dioxide / CH2Cl2 / 5 h / Ambient temperature
10: 69 percent / sodium hydroxide / methanol; H2O / 0.5 h / Ambient temperature
11: 6.56 g / manganese dioxide / CH2Cl2 / 2 h / Ambient temperature
With
manganese(IV) oxide; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; methanesulfonic acid; sulfuric acid; sodium methylate; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid;
In
tetrahydrofuran; pyridine; methanol; hexane; dichloromethane; water; acetic acid; acetone;
DOI:10.1021/jo00348a042
- Guidance literature:
-
Multi-step reaction with 9 steps
1: 1.) sodium methoxide / 2.) room temp., 16 h
2: 83 percent / sodium borohydride / methanol / 3 h / Ambient temperature
3: p-toluenesulfonic acid / tetrahydrofuran / 1 h / Ambient temperature
4: 68 percent / diisobutylaluminium hydride / tetrahydrofuran; hexane / 2 h / -20 - 0 °C
5: pyridine / 1 h / Ambient temperature
6: 72 percent / aq. H2SO4 / acetone / 1.5 h / Ambient temperature
7: 70 percent / manganese dioxide / CH2Cl2 / 5 h / Ambient temperature
8: 69 percent / sodium hydroxide / methanol; H2O / 0.5 h / Ambient temperature
9: 6.56 g / manganese dioxide / CH2Cl2 / 2 h / Ambient temperature
With
manganese(IV) oxide; sodium hydroxide; sodium tetrahydroborate; sulfuric acid; sodium methylate; diisobutylaluminium hydride; toluene-4-sulfonic acid;
In
tetrahydrofuran; pyridine; methanol; hexane; dichloromethane; water; acetone;
DOI:10.1021/jo00348a042
