Organic Lab Reactions 29

Organic Lab Reactions 29 - 24 THE CLAISEN REARRANGEMENT...

Info iconThis preview shows page 1. Sign up to view the full content.

View Full Document Right Arrow Icon
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-
Background image of page 1
This is the end of the preview. Sign up to access the rest of the document.

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.

Ask a homework question - tutors are online