Dichlorophenyl ether

A displacement of the chlorine atom has been observed in the rearrangement of allyl 2,6-dichlorophenyl ether (XLI), which is converted to the normal product (XLII, 60% yield) along with a little (10% yield) of 2-allyl-6-chlorophenol (XLIII).46 Some hydrogen chloride is evolved, also. 

Preparation of Allyl 2,4-Dichlorophenyl Ether.48 A mixture of 10.8 g. (0.066 mole) of 2,4-dichlorophenol, 9.7 g. (0.080 mole 21.5% excess) of allyl bromide, 9.4 g. of powdered anhydrous potassium carbonate, and 50 cc. of methyl ethyl ketone is refluxed for four and one-half hours. After cooling, 100 cc. of water is added and the organic layer is separated. The aqueous layer is extracted twice with 50-cc. portions of petroleum ether (b.p. 90-100°) and the extracts are combined with the organic layer, which is then extracted twice with 50-cc. portions of 10% sodium hydroxide to remove any unreacted phenol and washed twice with water. After drying over calcium chloride, the solvent is evaporated and the residual oil is distilled under diminished pressure, giving 11.4 g. 85%) of colorless liquid, b.p. 98-99°/2 mm. dfl 1.258 1.5522. 

Preparation of AUyl 2,4-Dichlorophenyl Ether.A mixture of 10.8 g. (0.066 mole) of 2,4-dichlorophenol, 9.7 g. (0.080 mole 21.5% excess) of allyl bromide, 9.4 g. of powdered anhydrous potassium carbonate, and 50 cc. of methyl ethyl ketone is refluxed for four and one-half hours. After cooling, 100 cc. of water is added and the organic layer is separated. 

Zitzelsberger, W., W. Ziegler, and P.R. Wallnofer. 1987. Stereochemistry of the degradation of veratrylglycerol-(3-2,4-dichlorophenyl-ether, a model compound for lignin bound xenobiotic residues by Phenerochaete chrysosporium, Corynebacterium equi and photosensitized rioboflavin. Chemosphere 16 1137-1142. 

Allyl 2,4-dichlorophenyl ether, MA copolymerization, 665 Allyl ether, ethoxylated lanolin, MA copolymerization, 532... 

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