Trisalicylide derivatives

Gnaim, J. M., Green, B. S., Aradyellin, R., Keehn, P. M., Improved preparation of the clathrate host compound triortho-thymotide and related trisalicylide derivatives. J. Org. Chem. 1991, 56, 4525-4529. 

B.S. Green and co-workers developed an improved preparation of the clathrate host compound tri-o-thymotide (TOT) and other trisalicylide derivatives. The synthesis began with the preparation of orfho-thymotic acid from thymol using the Kolbe-Schmitt reaction. The authors found that the yield of the product was dramatically increased when the reactants, solvents, and reagents were dried before use. Thus, thymol was dissolved in dry xylene, sodium metal was added and the temperature was kept at 130 °C for 20h in a dry carbon dioxide atmosphere. The desired carboxylated product was isolated in good yield. Finally, cyclodehydration with POCI3 afforded TOT in almost quantitative yield. 

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See also in sourсe #XX -- [ ]

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