A-Hydroxyphenylacetic acid

Figure 11.2.3 Structures of the hydroxybenzoic acids (A), hydroxyphenylacetic acid (B), and hydroxycinnamic acids (C). Also see UNIT 11.3.

Rule-based or systematic nomenclature (e.g., International Union of Pure and Applied Chemistry [IUPAC] or CAS nomenclature) is based on a set of linguistic rules that apply to its structure. For example, the IUPAC and CAS names for mandelic acid are 2-phenyl-2-hydroxyacetic acid and benzeneacetic acid, a-hydroxy-, respectively. The number of possible systematic names is practically endless. A small, but not nearly exhaustive, set of other systematic names includes phenylglycolic acid, phe-nylhydroxyacetic acid, ( )-a-hydroxybenzeneacetic acid, ( )-a-hydroxyphenylacetic acid, ( )-2-hydroxy-2-phenylethanoic acid, ( )-Mandelic acid, (RS)-Mandelic acid, DL-Amygdalicacid,DL-Hydroxy(phenyl)aceticacid,DL-mandelicacid,paramandelic acid, a-hydroxy- a-toluic acid, a-hydroxyphenylacetic acid, a-hydroxybenzeneacetic... 

HYDROXY-2-PHENOXYETHANE see PEROOO N-(4-HYDROXYPHENYL)ACETAMIDE see HIMOOO m-HAT)ROXYPHENYL ACETATE see RDZ900 a-HYDROXYPHENYLACETIC ACID see MAPOOO HYDROXYTHENYLACETONITRILE see MAP250... 

The kinetics of oxidation of substituted mandelic acids (a-hydroxyphenylacetic acid) in sulfate and mixed perchlorate/sulfate solutions are the subject of the four reports from Calvaruso et al. (1981a, b) and Arcoleo et al. (1977,1979). The oxidation reaction yields (substituted) benzaldehydes upon decarboxylation of mandelic acid. The oxidation of the p-nitro and p-methoxy derivatives in sulfuric acid proceeds without significant complex formation. The authors conclude that the reaction proceeds through two reactive Ce(IV) species,... 

Synonyms Amygdalic acid Amygdalinic acid Benzoglycolic acid Glycolic acid, phenyl- a-Hydroxyphenylacetic acid o-Hydroxy-a-toluic acid DL-Mandelic acid L-Mandelic acid Paramandelic acid Phenylglycolic acid... 

Mandelic acid a-Hydroxybenzeneacetic acid a-Hydroxyphenylacetic acid... 

A soln. of phenylacetic acid in dry tetrahydrofuran added dropwise at 0-5° to a stirred mixture of ca. 2 moles Li-diisopropylamide prepared from n-butyllithium and diisopropylamine in tetrahydrofuran-heptane, stirring continued 0.5 hr. at 0-5° then 1-1.5 hrs. at 40-50°, cooled to room temp., air bubbled ca. 18 hrs. into the soln., then ca. 2 volumes water added -> a-hydroxyphenylacetic acid. Y 66%. F. e. s. G. W. Moersch and M. L. Zwiesler, Synthesis 1971, 647. 

Moreover, an aerobic oxidative decarboxylative ammoxidation of phenylacetic acids and a-hydroxyphenylacetic acids to primary benzamides was realized with CU2O catalyst [28] (Scheme 3.10). The C(C=0)-N bond was formed with NH3 as nitrogen source and O2 as the sole terminal oxidant. Benzonitrile which is generated from phenylacetic acid through decarboxylation and ammoxidation with ammonia is the key intermediate for this transformation. It could convert into benzamide through ammonolysis and hydrolysis. A variety of primary benzamides could be prepared in 36-85 % yields form the corresponding acid. 

Song Q, Feng Q, Yang K (2014) Synthesis of primary amides via copper-catalyzed aerobic decarboxylative ammoxidation of phenylacetic acids and a-hydroxyphenylacetic acids with ammonia in water. Org Lett 16(2) 624-627... 

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