Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | N-Iodosuccinimide | HCID 120273 | — |
| Reactant | Cyclopentanone, 2-(1-hydroxypentyl)- | HCID 162060 | — |
| Solvent | Water | HCID 962 | — |
| Product | 2-Cyclopenten-1-one, 2-pentyl- | HCID 117549 | 85.6% |
Reaction Steps
In a 50 ml four-neck flask fitted with a thermometer, a reflux condenser and a stirrer were placed 2-(1-hydroxypentyl)cyclopentanone (20 g) synthesized in Reference Example 1, N-iodosuccinimide (0.1 g) and toluene (10 ml), and water was removed under refluxing, followed by 4 hours of the reaction at 150° C. The reaction mixture was washed with water and the layers were separated from each other. Further, the resulting organic layer was washed with saturated brine and separated. The organic layer was evaporated on a rotary evaporator under reduced pressure to recover toluene, whereby a crude product was obtained. The product was distilled using a Claisen distillation apparatus to obtain 15.3 g of 2-pentyl-2-cyclopentenone (boiling point: 104° C./930 Pa; GC purity: 98.4%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06833481B2 |
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| Source dataset | uspto-grants-2004_12 |
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| ORD ID | ord-4a1c660e7c0f4436ab040b4377e8448f |
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| Source note | uspto-grants-2004_12 |
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