24 THE CLAISEN REARRANGEMENT Ethers of higher boiling point frequently undergo undesirable side reactions when refluxed at atmospheric pressure, and often better yields are obtained by refluxing under diminished pressure.* The same result can be obtained more conveniently by mixing the ether with a solvent to act as diluent, the solvents most frequently employed being dimethylani-line (b.p. 193°) and diethylaniline (b.p. 215°). Better yields have been reported * with these basic solvents as compared to hydrocarbon sol-vents. 36 Kinetic studies of the rearrangement "• 68> 70 have shown that dimethylaniline has only a negligible effect on the rate, but it has been found 10 ° that dimethylaniline reduces polymerization during the rear-rangement of cinnamyl phenyl ether and greatly improves the yield. Paraffin oil,f tetralin, 47 and kerosene m have been employed as solvents with satisfactory results. The reaction mixture is usually worked up by removing the basic sol-
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This note was uploaded on 11/20/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.