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 Preparation of α-Ethyl-α-methylsuccinic acid
  • Preparation of α-Ethyl-α-methylsuccinic acid
  • α-Ethyl-α-methyl (CAS NO.: ), which is known as Succinic acid, α-ethyl-α-methyl-, could be produced through the following synthetic routes.

    Preparation of α-Ethyl-α-methylsuccinic acid

    cyanide (71.6 g., 1.1 moles, U.S.P.) and 100 ml. of 95% ethanol are placed in a 2-l. round-bottomed flask having a ground joint and arranged with a Hershberg stirrer. A solution of 113 g. (106 ml., 1 mole) of ethyl cyanoacetate, 79 g. (98 ml., 1.1 moles) of 2-butanone, and 66 ml. of glacial acetic acid is added to the stirred solution over a period of 1 hour. The mixture is stirred for an additional hour, the stirrer is removed, and the mixture is allowed to stand at room temperature for 7 days.

    Concentrated hydrochloric acid (500 ml.) is added to the semisolid reaction mixture, a reflux condenser is placed on the flask, and the mixture is heated under vigorous reflux for a period of 4 hours. An additional 500 ml. of hydrochloric acid is added, and the boiling under reflux is continued for an additional 4 hours.

    The cooled reaction mixture is extracted with four portions of ether (400 ml., 250 ml., 200 ml., 200 ml.) The ether extracts are filtered and combined, and about two-thirds of the ether is distilled. The ethereal solution is transferred to a 500-ml. Erlenmeyer flask, and the remaining ether is removed. The residue (about 160 g.) is dissolved in 200 ml. of 24% hydrochloric acid (1 part water, 2 parts concentrated hydrochloric acid) and the solution distilled until the boiling point reaches 108° The solution is cooled and allowed to stand at 5° for about 20 hours. The product is collected by vacuum filtration and dried in a vacuum desiccator containing both concentrated sulfuric acid and potassium hydroxide pellets. The yield of α-ethyl-α-methylsuccinic acid is 65–75 g. (41–47%), m.p. 91–97°. Concentration of the mother liquor to 125 ml. gives an additional 8–9 g. of acid, m.p. 85–91°.


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