HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethanol → 2,2-Dimethylcyclopentanone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | 4-Toluenesulfonyl chloride | HCID 7397 | — |
| Reactant | Hydroxyamine hydrochloride | HCID 443297 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Product | 2,2-Dimethylcyclopentanone | HCID 138286 | — |
| Product | 6,6-Dimethylpiperidin-2-one | HCID 1714407 | — |
Reaction Steps
The oxime of 2,2 dimethylcyclopentanone is prepared by reaction of the ketone with hydroxylamine hydrochloride in EtOH, and treated with p-toluenesulfonyl chloride and DMAP. Heating then effects Beckmann rearrangement to give 6,6-dimethyl-2-piperidinone which is deprotonated with NaH in DMF solution. Reaction with n-butyl iodide then gives the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05001113 |
| Source dataset | uspto-grants-1991_03 |
| ORD ID | ord-a010d9c3c9ea409e9b454f9466a6ce01 |
| Source note | uspto-grants-1991_03 |