Bromomandelic Acid

Ethyl see-butylidcnecyanoacetate has been prepared by this condensation using various amino acids,5 ammonium acetate,6 sodium sulfate-piperidine,7 and zinc chloride-aniline.8 

The ethyl 3-benzyl-2-cyano-3-methylpentanoate, 3-benzyl-3-methylpentanenitrile, and 3-benzyl-3-methylpentanoic acid preparations follow the procedure given by Prout, Huang, Hartman, and Korpics.9 

1 Department of Chemistry, De Paul University, Chicago 14, Illinois. 

2 Cason and Rapoport, Laboratory Text in Organic Chemistry, p. 312, Prentice-Hall, New York, New York, 1950 cf. Org. Syntheses Coll. Vol. 3, 601 (1955). 

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Note. Bromomandelic acid is a superior reagent for this determination, but is more expensive. A similar procedure to that above is employed. 

Bromides, D. of as silver bromide, (g) 491 by EDTA, (ti) 339 by mercury(I), (cm) 542 by oxygen flask, 113 by silver ion, (cm) 546 by silver nitrate, (ti) 351 by Volhard s method, (ti) 356 with iodide, (ti) 352 4-Bromomandelic acid 473 Bromophenol blue 265, 267 Bromopyrogallol red 182, 319 Bronsted-Lowry bases titration with strong acids, 277... 

Bromo-2-heptene, 38, 8 a-Bromoisobutyryl bromide, 33, 29 -Bromomandelic acid, 36,11 2-Bromo-3-methylbenzoic acid, 38,... 

Bromomandelic acid has been prepared by the bromination of -bromoacetophenone followed by alkaline hydrolysis 3 by the alkaline hydrolysis of the product formed by the addition of chloral to -bromophenylmagnesium bromide 4 and by the condensation of bromobenzene and ethyl oxomalonate in the presence of stannic chloride followed by hydrolysis and decarboxylation.5 />-Bromomandelic acid is a valuable reagent in the analyses of zirconium and hafnium.6... 

Zirconium can be co-precipitated with various metals as the arsenate [4]. Cupferron [with Fe(III) as a carrier] [5], oxine [6] and p-bromomandelic acid [7] have been used for selective separation of Zr (Hf). 

This reaction is, however, only of preparative use if the glyoxal derivative is itself obtained in a reaction carried out in alkaline solution, i.e., in the same batch. An example of this is provided by the preparation of p-bromomandelic acid from / ,co,eo-tribromoacetophenone recorded in Organic Syntheses 42... 

Merz used mandelic acid and p-bromomandelic acid with Y(ni) to carry Pu(in) quantitatively at pH 2-4 and above, Zirconium was used for Pu(IV) at higher acidities. The precipitation was about 85 0 complete at 1 M HCl and HNOg for p-... 

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