Allyl phenyl ether
Chemical compound
From Wikipedia, the free encyclopedia
Allyl phenyl ether is an organic compound with the formula C6H5OCH2CH=CH2. It is a colorless solid.
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| Names | |
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| Preferred IUPAC name
[(Prop-2-en-1-yl)oxy]benzene | |
| Other names
(Allyloxy)benzene 3-Phenoxypropene Allyloxybenzene | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.015.569 |
| EC Number |
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PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| 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: | |
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| Warning | |
| H302, H312, H332 | |
| 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).
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Preparation
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.
Reactions
Allyl phenyl ether converts to 2-allylphenol in the presence of acid catalysts. This conversion is an example of the Claisen rearrangement.[2][3]
