Evaluation of the Elbs Persulfate Oxidation Reaction for the Preparation of Aryloxyphenoxypropionate Herbicides

descriptionPublicationkeyboard_double_arrow_right Article 01 Aug 1995 English Publisher:CSIRO PublishingJournal:Australian Journal of Chemistry, volume 48, pages 1,503-1,509 (issn: 0004-9425, eissn: 1445-0038,

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Authors: KG Watson; A Serban;

doi: 10.1071/ch9951503

Evaluation of the Elbs Persulfate Oxidation Reaction for the Preparation of Aryloxyphenoxypropionate Herbicides

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Abstract

A new, simple method for the preparation of several 4-( aryloxy )phenols (2a-d) and alkyl 2-(4-hydroxyphenoxy)propionates (3a,b) is described. These compounds are key precursors for the synthesis of important aryloxyphenoxypropionate herbicides (1a-d). The method uses the Elbs persulfate oxidation to convert phenol into 4-hydroxyphenyl sulfate (5). The free hydroxy group is then reacted with various aryl halides and alkyl 2-halopropionates. Mild hydrolysis of the sulfate group with boiling acetic acid then gives the products (2a-d) and (3a,b), generally in modest to good yield.

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