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Synthesis of dimer and oligomers from ( R )‐methyl hydnocarpate
Author(s) -
Malkar Navdeep B.,
Vaidya Ashish A.,
Kumar V. G.
Publication year - 2000
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/s11746-000-0173-7
Subject(s) - oligomer , dimer , chemistry , cyclopentadiene , diastereomer , nuclear magnetic resonance spectroscopy , derivative (finance) , stereochemistry , organic chemistry , medicinal chemistry , catalysis , financial economics , economics
We 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, 1 H nuclear magnetic resonance (NMR), and 13 C NMR spectroscopic techniques.