Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetone | HCID 180 | — |
| Reactant | Hydroxide | HCID 961 | — |
| Reactant | Chlorobenzene | HCID 7964 | — |
| Reactant | Acetic acid, cyclopent-2-en-1-yl ester | HCID 140735 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | Cyclopentanol, acetate | HCID 70273 | 96% |
Reaction Steps
A solution of 1.80 g (0.014 mol) of 2-cyclopentenyl acetate in 3.80 g (0.12 mol) of methanol and 0.700 g of chlorobenzene (the internal standard for chromatographic analysis) was slowly passed through a jacketed column containing 20 ml of Dowex 1-X4 (an anion exchange resin of the quaternary ammonium type) in the hydroxide form in methanol. The column was maintained at 56° C. by refluxing acetone in the jacket. The resin was then rinsed with methanol, and the combined effluent and rinsings were analyzed by gas chromatography using a 6-ft. OV-17 column programmed from 80° to 220° C. The analysis showed that 2-cyclopentenol had been formed in 96% yield and essentially 100% efficiency. No by-products were observed.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04156097 |
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| Source dataset | uspto-grants-1979_05 |
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| ORD ID | ord-5911146e230d4528b94a170bd145a9dd |
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| Source note | uspto-grants-1979_05 |
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