:Allyl phenyl ether
{{Chembox
| ImageFile = Allyl phenyl ether.svg
| ImageSize = 200px
| PIN = [(Prop-2-en-1-yl)oxy]benzene
| OtherNames = (Allyloxy)benzene
3-Phenoxypropene
Allyloxybenzene
| Section1 = {{Chembox Identifiers
| CASNo = 1746-13-0
| PubChem = 74458
| ChemSpiderID = 21159535
| EC_number = 217-125-3
| UNII = 26S07OSX4O
| SMILES = C=CCOc1ccccc1
| StdInChI=1S/C9H10O/c1-2-8-10-9-6-4-3-5-7-9/h2-7H,1,8H2 COPY
| StdInChIKey = POSICDHOUBKJKP-UHFFFAOYSA-N
}}
| Section2 = {{Chembox Properties
| C=9|H=10|O=1
| Appearance = colorless solid
| Density =
| MeltingPtC = 90
| BoilingPtC = 191.7
| Solubility = }}
| Section3 = {{Chembox Hazards
| GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|302|312|332}}
| PPhrases = {{P-phrases|261|264|270|271|280|301+312|302+352|304+312|304+340|312|322|330|363|501}}
}}
}}
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:{{cite journal |doi=10.1021/ja01520a030|title=Heterogeneity as a Factor in the Alkylation of Ambident Anions: Phenoxide Ions1,2|year=1959|last1=Kornblum|first1=Nathan|last2=Lurie|first2=Arnold P.|journal=Journal of the American Chemical Society|volume=81|issue=11|pages=2705–2715}}
: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.{{cite journal |doi=10.1021/cr020703u|title=Claisen Rearrangement over the Past Nine Decades|year=2004|last1=Martín Castro|first1=Ana M.|journal=Chemical Reviews|volume=104|issue=6|pages=2939–3002|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
