Abstract
AbstractWe report synthesis and characterization of dimer and oligomer acids from chaulmoogra oil. (R)‐Methyl hydnocarpate (methyl ester of the major fatty acid component of chaulmoogra oil) was brominated to give threo‐2,3‐dibromocyclopentane‐1‐methyl undecanoate. Formation of two diastereoisomers, viz., threo‐2(R),3(R)‐dibromocyclopentane‐1(R)‐methyl undecanoate and threo‐2(S),3(S)‐dibromocyclopentane‐(R)‐1‐methyl undecanoate, was observed. Dehydrobromination of bromo derivatives using alcoholic KOH gave a cyclopentadiene derivative as intermediate, which underwent Diels‐Alder reaction to give dimer and oligomer fatty acids. The products were characterized by ultraviolet, direct exposure probe‐mass spectroscopy, 1H nuclear magnetic resonance (NMR), and 13C NMR spectroscopic techniques.
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