Wheat Bran Phenols 435 the above electrolysis the two products were separated by column chromatography and their identities were confirmed by comparison of their infrared spectra with those of authentic samples.Electrolysis of Propionic and Acetic Acids.-A mixture of propionic acid (6.8 g.), acetic acid (20 g.), and sodium acetate (2.1 g.) was electrolyzed as above (0.3 amp.) for a period of 6 hr. All material boiling below 120°was distilled directly from the reaction mixture, and the distillate was examined by gas chromatography using three different column packings. Peak enhancement, using authentic ethyl acetate, confirmed the presence of this ester, which was calculated to have been formed in about 13% yield from the propionic acid precursor.Electrolysis of 2,3,3-Triphenylpropanoic Acid. A. In Methanol.-2,3,3-Triphenylpropanoic acid2 (685 mg.) in methanol (20 ml.) containing sodium (26 mg.) was electrolyzed as above for a period of 17 min., after which the crude product was recovered by solvent evaporation. The residue was dissolved in ether, and the solution was extracted with dilute aqueous sodium hydroxide. Ether extraction of the acidified aqueous layer afforded 290 mg. of unchanged acid. Evaporation of the original ether layer yielded 351 mg. of crude product. This was chromatographed on acidwashed alumina (grade III, benzene-hexane eluent) to provide 172 mg. of white solid, m.p. 67.5-68°, after re crystallization from dilute methanol. The sample gave no mixture melting point depression, and displayed an infrared spectrum identical with that of authentic methyl 1,2,2-triphenylethyl ether. The latter sample, m.p. 66.5-68°, was prepared by the methylation of 1,2,2-triphenylethanol, as described before,28 using methyl iodide and silver oxide.
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