Additive-assisted Rupe rearrangement of 1-ethynylcyclohexan-1-ol in near-critical water
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Yong-Juan Chang
,
Zhi-Zhong Wang
Abstract
We performed the Rupe rearrangement of 1-ethynylcyclohexan-1-ol in near-critical water to study the reaction under high temperature conditions. The final product thus obtained was primarily 1-cyclohexen-1-ylethanone which was identified by GC-MS. The influences of reaction time, temperature, and initial reactant-to-water ratio on the yield of 1-cyclohexen-1-ylethanone were examined. The yield of 1-cyclohexen-1-ylethanone was 49 % in pure water at 260°C for a reaction time of 60 min. However, when additives such as ZnSO4, FeCl3, and NaHSO4, respectively, were introduced to the water to investigate the effect of salts on the Rupe rearrangement reaction, the yield increased markedly to as much as 88 % in 5 mole % NaHSO4 aqueous solution under the same conditions. The catalytic ability of the additives decreased in order: NaHSO4, FeCl3, ZnSO4. On the basis of these results, a possible reaction mechanism of the Rupe rearrangement of 1-ethynylcyclohexan-1-ol in near-critical water was proposed.
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© 2011 Institute of Chemistry, Slovak Academy of Sciences
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Articles in the same Issue
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- A novel reagent for spectroscopic determination of Mo(VI)
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- Application of 2-(octylsulphanyl)benzoic acid as Pb2+ selective ionophore in hybrid membrane system
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- Treatment of acidic palm oil for fatty acid methyl esters production
- Synthesis, structure, and luminescent properties of two novel polynuclear complexes of 1,3-di(pyridin-2-yl)propane-1,3-dione
- Mixed-ligand complexes of boric acid with organic biomolecules
- Ultrasound-assisted rapid synthesis of β-aminoketones with direct-type catalytic Mannich reaction using bismuth(III) triflate in aqueous media at room temperature
- Design, synthesis, preliminary pharmacological evaluation, and docking studies of pyrazoline derivatives
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