79688-36-1Relevant academic research and scientific papers
New application of triphosgene in a convenient synthesis of 3-aryl-1,3-benzoxazine-2,4-diones from anacardic acids
Sabioni Resck, Ines,dos Santos, Maria Lucilia,Soares Romeiro, Luiz Antonio
, p. 311 - 318 (2007/10/03)
In conjunction with a search program focused on utilization of cashew (Anacardium occidentale) nut shell liquid (CNSL) as starting material for the preparation of useful compounds, a convenient synthesis of novel series of 3-aryl-1, 3-benzoxazine-2, 4-diones was prepared from anacardic acids by using of the triphosgene.
Long-chain Phenols. Part 18. Conversion of Anacardic Acid into Urushiol
Kiong, Lam Soot,Tyman, John H. P.
, p. 1942 - 1952 (2007/10/02)
(15:0)-Anacardic acid (6-pentadecylsalicylic acid), prepared by reduction of unsaturated anacardic acid from Anacardium occidentale, has been converted into anacardic alcohol (6-pentadecylsalicylic alcohol) and thence by oxidation at carbon into anacardaldehyde.Phenolic oxidation of anacardic alcohol led to 8-pentadecyl-1-oxaspiroocta-5,7-dien-4-one, itself readily convertible photochemically, but less so thermally, into anacardaldehyde.Reaction of thionyl chloride with anacardic acid led mainly to the anhydride, which by hydride reduction gave anacardaldehyde less satisfactorily.Dakin oxidation of anacardaldehyde furnished (15:0)-urushiol (3-pentadecylcatechol) identical chemically and from argentation t.l.c. with the hydrogenated natural product from Rhus vernicifera. (15:0)-Cardanol (3-pentadecylphenol) has been detected in hydrogenated urushiol.The composition of the unsaturated constituents of urushiol from Rhus vernicifera and Rhus toxicodendron and its mode of formation have been discussed.An improved synthesis of (15:0)-urushiol has been devised based on an organo-lithium route.Aromatic methyl ether and ester formation in this series is greatly facilitated by phase-transfer catalysis.
