Allyl phenyl ether

Allyl phenyl ether is an organic compound with the formula C6H5OCH2CH=CH2. It is a colorless solid.

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
  • 217-125-3
UNII
  • InChI=1S/C9H10O/c1-2-8-10-9-6-4-3-5-7-9/h2-7H,1,8H2 COPY
    Key: POSICDHOUBKJKP-UHFFFAOYSA-N
  • C=CCOc1ccccc1
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:
GHS07: Exclamation mark
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).
Infobox references

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]

The Claisen rearrangement
The Claisen rearrangement

References
  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
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