Dolbier HW Solutions 598

Dolbier HW Solutions 598 - 692 PHENOLS The difculty with...

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The dif f culty with this route concerns the preparation of diphenyl ether. Direct reaction of phenox- ide ion with chlorobenzene is very slow and requires high temperatures because chlorobenzene is a poor substrate for nucleophilic substitution. A third route is also unsatisfactory because it, too, requires nucleophilic substitution on chlorobenzene. 24.22 The overall transformation that needs to be effected is A reasonable place to begin is with the attachment of the side chain. The aldehyde function allows for chain extension by a Wittig reaction. Hydrogenation of the double bond and hydrogen halide cleavage of the ether functions complete the
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This note was uploaded on 10/03/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.

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