- Preparation of Ethyl enanthylsuccinate
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Ethyl enanthylsuccinate could be produced through the following synthetic routes.
A mixture of 228 g. (2.0 moles) of enanthaldehyde and 172 g. (1.0 mole) of ethyl maleate is placed in a jacketed flask (Fig. 9) with condensers attached to the flask and the jacket openings. The jacket is charged with trichloroethylene, which is heated to reflux, and, when the reaction mixture reaches 84–85°, 0.5 g. of benzoyl peroxide is added to the mixture through the condenser. After 3–8 hours an additional 0.5-g. portion of benzoyl peroxide is added, and heating is continued for a total of 18–24 hours.
Fig. 9.
The reaction mixture is distilled through a short (8- to 12-in.) Vigreux column to give 108–111 g. of recovered enanthaldehyde, b.p. 64–65°/38 mm.; 6–16 g. of an intermediate fraction, b.p. 82–128°/1 mm.; and 202–216 g. (71–76% yield) of ethyl enanthylsuccinate, b.p. 119–122°/0.7 mm., nD25 1.4392–1.4398.
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