Patent ID: 6579992
Filing Date: 2003-06-17
Classification: C07C

Abstract:
A method for preparing coconut flavored, two chiral centered, 5-isobutyl-3-methyl-4,5-dihydro-2(3H)-furanone, comprising:a. adsorbing Tagetes minuta oil onto an adsorbent; b. loading said Tagetes minuta oil-adsorbed adsorbent into a soxhlet extractor and washing said adsorbent with a non-polar solvent; c. isolating dihydrotagetone-rich fractions using hot hexane percolation with increasing percentages of ethylacetate starting from 0.2 up to 5%; d. concentrating said fractions under reduced pressure to obtain a dihydrotagetone rich concentrate; e. loading said concentrate onto an alumina or silica gel column and eluting the column with a non polar solvent; f. further eluting said column using increasing percentages of ethyl acetate up to 5% in hexane; g. concentrating the resulting hexane-ethylacetate fractions under reduced pressure to obtain purified dihydrotagetone; and h. oxidizing the purified dihydrotagetone, recovering resultant 2,6-dimethyl-4-oxo-heptanoic acid, reducing the 2,6-dimethyl-4-oxo-heptanoic acid, and converting the reduced product to 5-isobutyl-3-methyl-4,5-dihydro-2(3H)-furanone, wherein the 5-isobutyl-3-methyl-4,5-dihydro-2(3H)-furanone is coconut flavored and possesses two chiral centers.