In the high-dilution Friedel-Crafts reaction: 6-phenylhexanoyl chloride gave I (re = 5) in 67% yield; 6-(3,5-dimethylphenyl)-hexanovl chloride gave IV in 54% yield; 7-phenylheptanoyl chloride gave a 5% yield of dimeric ketone, V7, and a 0.4% yield of trimer, VI; 8-phenyloctanoyl chloride gave a trace of unidentified crystalline product in addition to polymer; 10-phenyldecanoyl chloride gave a small yield of paracyclanone, VII, and the dimer, VIII. It was confirmed5 from spectral data that the phenyl and carbonyl groups of I (re = 5) are not completely conjugated. Resonance is inhibited much more in the oxime of I (re = 5). There is nearly complete inhibition of phenyl-carbonyl interaction in IV7, and a slight inhibition in VII.All the other ketones prepared appear to be completely conjugated. A shift in Xma, in the ultraviolet spectrum of V7 is interpreted in terms of a spatial interaction of the two conjugated systems such as could occur in configuration VA. Compound IV gives the deacylation reaction, whereas I (re = 5) does not. Attempts to obtain diastereoisomers of the Zmenthydrazone of I (re = 5) led to inconclusive results.

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Conclusion and SummaryA laboratory process has been developed for the continuous countercurrent preparation of epoxidized oils. This consists of introducing continuously, to a packed column, an unsaturated oil, hydrogen peroxide, and acetic acid, and withdrawing the epoxidized product. Operating variables have been investigated and optimum conditions predicted. Obtainment of maximum yields must await construction of a longer column.