HuagongsheHuagongshe Chemistry Print Report · For research reference only
p-Toluenesulfonic acid → HCID 59226560, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | p-Toluenesulfonic acid | HCID 6101 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | 5-Methyl-3-(3-nitropyridin-4-yl)cyclohex-2-enol | HCID 67130710 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 59226560 | HCID 59226560 | 68% |
Reaction Conditions
| Temperature | 100 °C |
|---|
Reaction Steps
To a solution of 5-methyl-3-(3-nitropyridin-4-yl)cyclohex-2-enol (1.0 equiv.) in dioxane (0.1M) was added p-TSA (1.0 equiv.), and the reaction was stirred at 100° C. for 3 h. The solution was cooled to room temperature, then passed through a pad of neutral alumina eluting with EtOAc to yield (+/−)-4-(5-methylcyclohexa-1,3-dienyl)-3-nitropyridine as a yellow oil in 68% yield. LC/MS=217.1 (M+H), LC=3.908 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08168794B2 |
| Source dataset | uspto-grants-2012_05 |
| ORD ID | ord-305cbb8b18b1417480f8e36258997f47 |
| Source note | uspto-grants-2012_05 |