Campbell, Neil published the artcilePreparation of the halophenylacetic acids, Quality Control of 13312-84-0, the publication is Journal of the Chemical Society (1948), 1251-5, database is CAplus.
Gränacher’s synthesis (C.A. 16, 3898; 17, 2424) has been applied to the preparation of XC6H4CH2CO2H; the method depends on a satisfactory preparation of rhodanine (I), which is discussed. The yield of I depends upon the yield of H2NCSSNH4 (II) in the 1st stage of the reaction; the yield of II, as compared with that of CS(SNH4)2 (III), is a function of the NH3 concentration which, in turn, is dependent on the temperature The more concentrated the NH3 solution, the greater is the yield of III; the best yield of II is obtained at 10-15°; the yield of I from II is 44%. When the temperature is kept below 0%, III is the main product. Methods of distinguishing between II and III are given. Mol. quantities of aldehyde and I in AcOH (5 cc. per g. aldehyde), refluxed 0.5 h. with fused AcONa (twice the weight of I), give the following benzylidenerhodanines (IV): ο-Cl, pale yellow, m. 192°, 97% (Andreasch, C.A. 22, 3410, gives 169°); m-Cl, pale yellow, m. 233°, 93%; p-Cl, yellow, m. 231-2°, 93%; ο-Br, orange, m. 183.5°, 80%; m-Br, yellow, m. 238°, 90%; p-Br, yellow, m. 237-8°, 84%. IV were transformed into β-phenyl-α-thiopyruvic acids (V) by heating with 8 cc. 8% NaOH (per g. IV) at 50-5° until a clear or nearly clear solution resulted, cooling in an ice-salt bath, and acidifying rapidly with 3 N HCl; the crude acid in cold EtOH is precipitated with 1-2 volumes cold H2O and recrystallized from MeOH, petr. ether, etc.; however, the crude acids were used in the next step. ο-Cl, m. 134-5°, 72% (A. gives 119-20°); m-Cl, straw-colored, m. 134°, 84%; p-Cl, yellow, m. 169-71°, 84% [a byproduct is probably α,α’-dithiobis(m-chlorocinnamic acid), yellow, m. 221-2°]; ο-Br, lemon-yellow, m. 142-3°, 70%; m-Br, pale yellow, m. 133-4°, 81%; p-Br, m. 165-80°, 75% (could not be purified further). α-Isonitroso-β-(halophenyl)propionic acids (VI) were prepared from V by refluxing (about 0.5 h.) in alc. containing 3 mols. NH2OH (until H2S evolution ceases); the crude acid is precipitated from dilute NaOH solution with concentrated HCl. ο-Cl, m. 156°, 83%; m-Cl, m. 149° (decomposition), 100%; p-Cl, m. 170° (decomposition) (1 sample m. 182°), 100%; ο-Br, m. 150° (decomposition), 100%; m-Br, m. 151°, 93%; p-Br, m. 173°, 85% (yields are of crude products). VI, refluxed 10 min. with Ac2O (4 cc. per g. VI), the Ac2O removed in vacuo, and the residue extracted with ether, give the (halophenyl)acetonitriles (VII): ο-Cl, b11 123-5°, 64%; m-Cl, b10 134-6°, 55%; p-Cl, b12 137-9°, m. 31-2°, 80%; ο-Br, b13, 140-1°, 88%; m-Br, b10 145-7°, m. 27-8°, 70%; p-Br, b10-12 152-6°, m. 48°, 72%. The over-all yields of the VII from the aldehydes were: ο-, m-, and p-Cl, 57, 47, 62%; ο-, m-, and p-Br, 49, 44, 38%; further losses, sometimes considerable, occur in the next step. VII were hydrolyzed by boiling with 60% H2SO4 or, preferably, with 20% EtOH-KOH, giving RC6H4CH2CO2H (R given): ο-Cl, m. 93-5° (p-nitrobenzyl ester, m. 70-1°); m-Cl, m. 77° (p-nitrobenzyl ester, m. 74-5°; p-toluidide, m. 138°); p-Cl, m. 104-6° (p-nitrobenzyl ester, m. 117°); ο-Br, m. 104-5° (p-nitrobenzyl ester, m. 74-5°; p-toluidide, m. 183-4°; anilide, m. 153-4°); m-Br, m. 102-3° (p-nitrobenzyl ester, m. 75-6°; p-toluidide, m. 135°); p-Br, m. 113-15° (p-nitrobenzyl ester, m. 128-9°; anilide, m. 174-6°; p-toluidide, m. 203°). The results show that this method leaves much to be desired. The crystalline compound from 20 g. p-BrC6H4CHO, 80 cc. NaHSO3, and 5 cc. EtOH, stirred 2 h. with 10 g. KCN in 20 cc. H2O, gives 12.5 g. p-bromomandelonitrile, m. 78-9°; 11 g. and 46 cc. HI (d. 1.94), refluxed 1 h. give 1.5 g. p-BrC6H4CH2CO2H; an unknown compound, m. 126-7°, is a byproduct. ο-ClC6H4CHO, through ο-ClC6H4CH(OH)CN, yields the benzoate (no properties given); refluxing with Pt black in tetralin did not give ο-ClC6H4CH2CN. p-MeOC6H4CH2CN was obtained in 39% yield (yield of intermediate benzoate 74 and 92% in 2 experiments). Other methods were tried without much success. A mixture of ο- and p-BrC6H4CH2CO2H could not be separated by fractional distillation of the acid chlorides or Et esters; chromatog. separation of the anilides, p-toluidides, and 2-naphthalides was only partially successful (they fluoresce in C6H6 but not on the Al2O3 column). α-(ο-Bromophenyl)aceto-2-naphthalide, m. 188-9°; p-isomer, m. 203-4°. α-Phenylaceto-2-naphthalide m. 162-3°. In the preparation of the naphthalides by heating the acids with 2-C10H7NH2, (2-C10H7)2NH is obtained, the catalyst presumably being the halo acid. 2-C10H7NH2 and PhNH2 give 2-C10H7NHPh, and p-MeC6H4NH2 gives 2-C10H7NHC6H4Me-p, but ο- or m-ClC6H4NH2 gives only (2-C10H7)2NH. 2-C10H7NH2 and its derivatives are more strongly adsorbed than the corresponding 1-derivatives
Journal of the Chemical Society published new progress about 13312-84-0. 13312-84-0 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Alcohol,Benzene Compounds, name is 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, and the molecular formula is C8H6ClNO, Quality Control of 13312-84-0.
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https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts