Abstract
Aqueous chlorination of linoleic acid gave a mixture of tetrachlorostearic acid, trichlorohydroxystearic acid and dichlorohydroxystearic acid of linoleic acid in relative percentages of 49%, 38% and 13% respectively. Treatment of threo- cis- cis-9,10,12,13-diepoxystearic acid with HCl gave a mixture of tetrahydrofuranyl ethers and dichlorohydrins in relative percentages of 24% and 76%. A separate synthesis of trichlorohydroxystearic acid is described. Products were identified by infrared spectrometry (IR), nuclear magnetic resonance spectroscopy (NMR) and negative methane chemical ionization mass spectrometry (NCl). Chlorohydrins were confirmed by their conversion to epoxides by NaOH.
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