HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetaldehyde → HCID 67528997, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetaldehyde | HCID 177 | — |
| Reactant | p-Toluenesulfonic acid monohydrate | HCID 521998 | — |
| Reactant | Sodium ethoxide | HCID 2723922 | — |
| Reactant | Lithium diisopropylamide | HCID 2724682 | — |
| Reactant | HCID 67528778 | HCID 67528778 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Cyclohexane | HCID 8078 | — |
| Product | HCID 67528997 | HCID 67528997 | — |
Reaction Steps
A crude 80:20 mixture of 1-(rel-(1S,2S,6S)-/1-(rel-(1R,2S,6S)-2-ethyl-6-methylcyclohex-3-enyl)ethan-1-one (2.6 g) was prepared as described in Example 2 by EtONa catalyzed epimerization of 1-(rel-(1R,2S,6S)-2-ethyl-6-methylcyclohex-3-enyl)ethan-1-one (3.15 g, 18.9 mmol, Example 3) in ethanol (30 ml) at reflux (25 h). Aldolisation (LDA, AcH, THF) and water-elimination (PTSA.H2O, cyclohexane, reflux, 45 min.) gave a 83:17 mixture of 1-(rel-(1S,2S,6S)-/1-(rel-(1R,2S,6S)-2-ethyl-6-methylcyclohex-3-enyl)ethan-1-one (1.27 g, 2 steps: 42%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07812195B2 |
| Source dataset | uspto-grants-2010_10 |
| ORD ID | ord-19a03036a3614ca0bd92a6f5be0a3bad |
| Source note | uspto-grants-2010_10 |