Allyl phenyl ether

Allyl phenyl ether
Names
	Preferred IUPAC name [(Prop-2-en-1-yl)oxy]benzene
	Other names (Allyloxy)benzene; 3-Phenoxypropene; Allyloxybenzene
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 COPY Key: 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

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]

References

^ 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

[1] 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.

[2] Martín Castro, Ana M. (2004). "Claisen Rearrangement over the Past Nine Decades". Chemical Reviews. 104 (6): 2939–3002. doi:10.1021/cr020703u. PMID 15186185.

[3] 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

[1]

[2]

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