Allyl phenyl ether
Names | |
---|---|
Preferred IUPAC name
[(Prop-2-en-1-yl)oxy]benzene | |
Other names
(Allyloxy)benzene
3-Phenoxypropene Allyloxybenzene | |
Identifiers | |
3D model (
JSmol ) |
|
ChemSpider | |
ECHA InfoCard
|
100.015.569 |
EC Number |
|
PubChem CID
|
|
UNII | |
CompTox Dashboard (EPA)
|
|
| |
| |
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: | |
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).
|
Allyl phenyl ether is an organic compound with the formula C6H5OCH2CH=CH2. It is a colorless solid.
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]