SUMMARY
Lemon oil was analyzed on a highly efficient modified Apiezon L open tubular column with a single injection. Almost all of the more than forty individual peaks were identified by comparison of mass spectra and retention times with those of known compounds. Lemon oils from throughout the world were found very similar in their gas chromatograms; differences were primarily quantitative rather than qualitative.
SUMMARY
Recent refinements in thin‐layer chromatography (TLC) provide the analytical chemist with an inexpensive, convenient, and rapid method for obtaining basic information on the condition of cold‐pressed citrus oil samples. Simple TLC distinguished lemon and lime oils from all other citrus oils. Two‐dimensional TLC was used to distinguish between lemon and lime oils. Distilled lemon oils were characterized by their deficiency of UV fluorescence.
Reaction of n-butylmagnesium bromide with an approximately equimolar amount of 2-(/3-cyanoethyI)-2-ethylhexanal at 0°in diethyl ether as solvent yields about equal amounts of the reduction product, 2-(0-cyanoethy 1 )-2-ethyl-1-hexanol (II), and the addition product, 6-(/3-cyanoethyl)-6-ethyl-5-decanol (III). There could be detected no product resulting from reaction of the nitrile grouping. Yields were similar, whether normal addition or inverse addition was used in the reaction. In anisóle as solvent, considerable quantities of two unidentified by-products could be detected by gas phase chromatography, and the yield of the addition product, III, was somewhat lower. With inverse addition in anisóle, the amount of reduction was much greater than observed when diethyl ether was the solvent. The addition product, the cyano alcohol III, was hydrolyzed to a lactone which was transesterified with methanol to yield a mixture of unsaturated esters. Ozonolvsis of these esters indicates the mixture expected from rearrangement of the carbonium ion resulting from alkyl-oxvgen fission of the lactone, and development of the double bond at less substituted positions as well as the most substituted position.
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