Allyl phenyl ether (original) (raw)
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Allyl phenyl ether
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| Names | |
| Preferred IUPAC name [(Prop-2-en-1-yl)oxy]benzene | |
| Other names(Allyloxy)benzene3-PhenoxypropeneAllyloxybenzene | |
| Identifiers | |
| CAS Number | 1746-13-0 |
| 3D model (JSmol) | Interactive image |
| ChemSpider | 21159535 |
| ECHA InfoCard | 100.015.569  |
| EC Number | 217-125-3 |
| PubChem CID | 74458 |
| UNII | 26S07OSX4O |
| CompTox Dashboard (EPA) | DTXSID6061943 |
| InChI InChI=1S/C9H10O/c1-2-8-10-9-6-4-3-5-7-9/h2-7H,1,8H2 COPYKey: POSICDHOUBKJKP-UHFFFAOYSA-N | |
| SMILES C=CCOc1ccccc1 | |
| Properties | |
| Chemical formula | C9H10O |
| Molar mass | 134.178 g·mol−1 |
| Appearance | colorless solid |
| Melting point | 90 °C (194 °F; 363 K) |
| Boiling point | 191.7 °C (377.1 °F; 464.8 K) |
| Hazards | |
| GHS labelling: | |
| Pictograms |  |
| Signal word | Warning |
| Hazard statements | H302, H312, H332 |
| Precautionary statements | P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P322, P330, P363, P501 |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references |
Chemical compound
Allyl phenyl ether is an organic compound with the formula C6H5OCH2CH=CH2. It is a colorless solid.
Allyl phenyl ether is prepared by the reaction of sodium phenoxide with allyl bromide:[1]
C6H5ONa + BrCH2CH=CH2 → C6H5OCH2CH=CH2 + NaBr
The yield is almost quantitative when the reaction is conducted in homogeneous solution using dimethoxyethane. When the reaction is conducted as a slurry in diethyl ether, the predominant product is, after acidic work-up, 2-allylphenol.
Allyl phenyl ether converts to 2-allylphenol in the presence of acid catalysts. This conversion is an example of the Claisen rearrangement.[2][3]
The Claisen rearrangement
- ^ Kornblum, Nathan; Lurie, Arnold P. (1959). "Heterogeneity as a Factor in the Alkylation of Ambident Anions: Phenoxide Ions1,2". Journal of the American Chemical Society. 81 (11): 2705–2715. doi:10.1021/ja01520a030.
- ^ Martín Castro, Ana M. (2004). "Claisen Rearrangement over the Past Nine Decades". Chemical Reviews. 104 (6): 2939–3002. doi:10.1021/cr020703u. PMID 15186185.
- ^ Yadav, G. D.; Lande, S. V., UDCaT-5: A Novel and Efficient Solid Superacid Catalyst for Claisen Rearrangement of Substituted Allyl Phenyl Ethers. Synthetic Communications 2007, 37 (6), 941-946