Ethylene adduct of conjugated octadecadienoic acids: II. Ozonization products View Full Text


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Article Info

DATE

1970-02

AUTHORS

E. J. Dufek, J. C. Cowan, J. P. Friedrich

ABSTRACT

Methyl 8-(4-n-hexylcyclohex-2-enyl) octanoate obtained by esterifying the adduct of ethylene andtrans,trans-9,11-octadecadienoic acid was ozonized in methanol as a participating solvent. The resultant cyclic methoxyhemiperacetal was reduced with powdered zinc to the dialdehyde, methyl 9,12-diformylstearate, which was isolated as the tetramethyldiacetal. This dialdehyde readily air-oxidizes to give methyl 9,12-dicarboxystearate. Heating the cyclic methoxyhemiperacetal slowly from 25 to 100 C in vacuo results in an unusual decomposition reaction which gives hydrogen and methyl 9 (12)-carbomethoxy-12(9)-carboxystearate as the primary products and methyl 9 (12)-carbomethoxystearate as the major by-product. Treatment of the cyclic hemiperacetal with hydrogen peroxide in formic acid gave unexpectedly dihydroxystearic acid as one of the products. More... »

PAGES

51-55

References to SciGraph publications

  • 1966-05. Infrared spectrophotometric procedure for determining azelaaldehydic acid derivatives in JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY
  • 1965-10. A comparison of participating solvents during ozonization in JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY
  • 1969-03. Hydroformylation of unsaturated fatty esters in JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY
  • 1962-09. Reaction of ethylene with C18 monocarboxylic dienoic acids in JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY
  • 1966-01. Reduction of methyl oleate ozonolysis products to aldehydes with activated zinc in JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY
  • Identifiers

    URI

    http://scigraph.springernature.com/pub.10.1007/bf02541457

    DOI

    http://dx.doi.org/10.1007/bf02541457

    DIMENSIONS

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