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
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

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