Phenoxybutyric acids

Phenoxybutyric acid [6303-58-8] M 180.2, m 64", 65-66", 82-83", 99", b 180-185"/ 2mm, pK 3.17. It has been purified by recrystn from pet ether, C6H6, Et20-pet ether, EtOH and from H2O. It can be steam distd or distd in a good vac. [UV Ramart-Lucas and Hoch Bull Soc Chim Fr [4] 51 824 1932, Dann and Arndt Justus Liebigs Ann Chem 587 38 1954.] The acid chloride has b 154-156°/20mm [Hamford and Adams J Am Chem Soc 57 921 1935], and the amide crystallises from C6H6 as needles m 113°. 

Chau and Terry [146] reported the formation of penta-fluorobenzyl derivatives of ten herbicidal acids including 4-chloro-2-methyl-phenoxy acetic acid [145]. They found that 5h was an optimum reaction time at room temperature with pentafluorobenzyl bromide in the presence of potassium carbonate solution. Agemian and Chau [147] studied the residue analysis of 4-chloro-2-methyl phenoxy acetic acid and 4-chloro-2-methyl phenoxy butyric acid from water samples by making the pentafluorobenzyl derivatives. Bromination [148], nitrification [149] and esterification with halogenated alcohol [145] have also been used to study the residue analysis of 4-chloro-2-methyl phenoxy acetic acid and 4-chloro-2-methyl phenoxybutyric acid. Recently pentafluorobenzyl derivatives of phenols and carboxylic acids were prepared for detection by electron capture at very low levels [150, 151]. Pentafluorobenzyl bromide has also been used for the analytical determination of organophosphorus pesticides [152],... 

Carboxylic acids, acyl chlorides, and sulfonyl chlorides used for deri-vatization of 4-aminophenylalanine and >-4-am i n op h e ny I a I a n i n e are as follows 5-hydantoinacetic acid, / ran, v - 4 - co t i n i n ec a r b o xy I i c acid, isonicotinic acid, 3-pyridinepropionic acid, 4-hydroxyphenylacetic acid, 2-butynoic acid, 2-pyrazinecarboxylic acid, cyclopropanecarboxylic acid, 3-hydroxy-2-qui-noxaline carboxylic acid, 5-bromovaleric acid, propargyl chloroformate, 3,4-dimethoxybenzoyl chloride, 2-thiophenesulfonyl chloride, 3-thiophene-carboxylic acid, 2-thiophenecarboxylic acid, 2-methylbutyric acid, 2-thio-pheneacetyl chloride, benzoic acid, furylacrylic acid, 4-nitrophenyl acetic acid, 2,5-dimethoxyphenylacetic acid, p-toluenesulfonyl chloride, 4-(di-methylamino)phenylacetic acid, 3-indolepropionic acid, phenoxyacetic acid, 3-(dimethylamino)benzoic acid, cyclohexanecarboxylic acid, naphtha-lenesulfonyl chloride, 4-bromophenylacetic acid, 4-bromobenzoic acid, 2-phenoxybutyric acid, 3,4-dichlorophenylacetic acid, (l-naphthoxy)acetic acid. 

The fragmentation pathways for the methyl esters are strongly dependent on the type of acid, i.e. whether a derivative of phenoxyacetic acid, phen-oxypropionic acid, or phenoxybutyric acid, and on the nature of the substitution of the aromatic ring. The methyl esters of chlorinated phenoxyacetic and phenoxypropionic acids show reasonably abundant molecular ions (about 20% relative to the base peak) which, together with the chlorine isotope patterns, permit easy identification of these compounds. In contrast, the spectra of the methyl esters of chlorinated phenoxybutyric acids are dominated by the fragment ion at m/z 101, with only low abundance of molecular ions. However, the spectra also show... 

The preparation of y-phenoxybutyric acid (61%) by acid hydrolysis of the phenoxycyanide is a typical example of the formation of an ether acid by this method. Nine alkoxypropionic acids, ROCH CHjCOjH, have been made in 4S> 86% yields by acid hydrolysis of the alkoxy nitriles. Basic hydrolysis gives readily polymerizable material propably because of partial decomposition of the alkoxy nitrile into the alcohol and acrylonitrile. ... 

The reverse situation - selective bioactivation in the uneconomic species — is realized in the selectively acting weedkillers of the phenoxybutyric acid type (Fig. 8). The butyric acid derivatives, as such, are inactive they have to be converted by 0-oxidation to the corresponding phenoxyacetic acid derivatives, which have the required auxin and hence weedkiller action. Since plant species... 

Three y-phenoxybutyric acids are used as herbicides in agriculture. 

Three phenoxybutyric acid derivatives have been developed for agricultural use ... 

Three synthesis routes are known for the preparation of phenoxybutyric acid derivatives (Melnikov, 1971). 

Shapiro and co-workers [260, 261] reported the preparation of a large number of 2-phenoxybutyric acid derivatives which were tested for hypo-cholesterolemic activity in the guinea-pig. The most active compound in their first series of -acetamido-phenoxyacetic acid derivatives was XCIII. 

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