Chloro acetic acid

Salicylaldehydc, reaction with chloro-acetic acid, 46,28... 

In a 5-I. round-bottomed flask, 500 g. (5.3 moles) of chloro-acetic acid (Note 1) is dissolved in 700 cc. of water. The solution is warmed to 50°, neutralized with 290 g. (2.7 moles) of anhydrous sodium carbonate, and again cooled to room temperature. Meanwhile, 294 g. (6.0 moles) of sodium cyanide (97 per cent) is dissolved in 750 cc. of water warmed to 55°, the solution is cooled to room temperature, and then added to the sodium chloroacetate solution, with rapid mixing of the two solutions and cooling under the water tap. When the solutions are completely mixed, the cooling is stopped and the temperature allowed to rise. When it reaches 95° the solution is cooled by adding 200 cc. of ice water, and this is repeated, if necessary, until the temperature no longer rises (Note 2). The solution is then heated on the steam bath for one hour to ensure completion of the reaction. 

In a 2-1. flask provided with a mechanical stirrer, separatory funnel, and thermometer, are placed 189 g. (2 moles) of chloro-acetic acid and 150 cc. of water. The flask is cooled in ice water, and a cold solution of 160 g. (4 moles) of sodium hydroxide in 500 cc. of water is added, with stirring, at such a rate that the temperature does not exceed 30° (Note 1). AfLer all the alkali has been added, the cooling bath is removed, and an aqueous solution (Note 2) containing 31 g. (1 mole) of methylamine is added slowly. The reaction is exothermic, and the temperature is kept below 50° by occasional immersion of the flask in ice water. After all the methylamine has been added, the solution is allowed to stand for two hours to complete the reaction. 

Answer Friedel-Crafts disconnection reveals 1,2-diX compound (21) easily made from thiol (22) and chloro-acetic acid. Thiol (22) can be made by the thiourea route (p T 37 ). 

The a-halogenated carboxylic adds, of which the simplest is chloro-acetic acid, are widely used in synthesis. Their conversion into hydroxy-acids (by hydrolytic elimination of the halogen) and into aminoacids (p. 275) may be mentioned here ... 

The ammonium -chlorophenyldithiocarbamate obtained is transferred immediately to a 1-1. beaker fitted with an efficient mechanical stirrer. Water (250 ml.) is added, and the temperature is raised to 30°. A solution of 28.4 g. (0.30 mole) of chloro-acetic acid in 30 ml. of water is neutralized with sodium carbonate [18.6 g. (0.15 mole) of Na2C03-H20 in 70 ml. of water] and is added to the weU-stirred dithiocarbamate suspension over a 10-minute period (Note 3). In the beginning the suspension gradually becomes less viscous, but at the end of the addition it rapidly turns into a creamy mass. Another 250 ml. of water is added to facilitate stirring, which is continued for 1 hour after the addition at about 30°. 

Cellulose Etherification with chloro-acetic acid (carboxymethylation) Carboxymethyl cellulose 5-6 HW 2042 K 1521... 

An example of anomalous behavior in closely related systems was reported some time ago during an investigation of the cychzation products derived from coumarin semicarbazones (Scheme 6.21). Thus, 78a reacted cleanly with chloro-acetic acid to yield 79a, which cyclized to the expected product 80a upon treatment with sodium acetate. On the other hand, 79b did not cyclize under the same reaction conditions. This was attributed to the absence of the enolizable hydrogen (Ph vs. H). The authors did not comment on the possibility of cyclization of 79b to 80b. The closely related urea analogue 81 did not react with chloroacetic acid thereby... 

Carboxymethyl starch (with mono chloro acetic acid)... 

C 2H, C1N2OkS 97764-69-7) sec Carumonam 2-chloro-acetic acid (2-((mcthylamino)methyl phcnyl]-pheny lmcthyl tester... 

Refluxing of 2,5-bis[phenylhydroxymethyl]tellurophene and pyrrole in benzene/chloro-acetic acid (98 2) gave rise to 2,5-bis phenylpyrrolylmethylene]-2,5-dihydrotellurophene, which, in turn, was reacted with 2,5-bis[phenylhydroxymethyl]thiophene. Tetraphenyl-21-tellura-23-thiaporphyrin was isolated in 0.07% yield3. 

Acetic acid dodine, fentin, glyodin, phenyl mercury acetate, see acetyl chloride chloro acetic acid... 

Methyl thiophenol fensulfothion, sulfoprofos Methyl thiopseudo urea guazatine, hexazinone 4 Methyl thiosemi carbazide thiazafluron Methyl thio urea tebuthiuron, thiazafluron Monobromo benzene chlorbromuron Monochloro acetic acid see Chloro acetic acid Morpholine dimethomorph, ethofumesate, nipyraclofen Mucochloric acid chloridazon, norflurazon, pyridaben... 

Catalytic rate coefficients for iodination of aliphatic aldehydes in chloro-acetic acid-chloroacetate ion buffers11... 

Direct chlorination of acetic acid in the presence of a small quantity of red phosphorus is a standard procedure for the preparation of chloro-acetic acid however, similar treatment of its straight-chain homologs gives complex mixtures of halogenated acids. Substitution by chlorine in a btanched-chain acid such as isovaleric acid occurs largely at the tertiary hydrogen. The peroxide-catalyzed chlorination of aliphatic acids... 

Reaction of benzofuro[2,3-y]benzimidazole-2-thione (423) with chloro-acetic acid gives acid 424 which, on cyclization with acetic anhydride, yields a cyclized product for which structure thiazolo[2, 3 -(>]benzofuro [2,3-/]benzimidazol-3(2/y)-one (425) was assigned (77M12) however, alternate structure 426 cannot be ruled out in the absence of adequate data (Scheme 97). 

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