Nohr-McDonald elimination reaction

McDonald etal, US Patent 6,211,383 (April 3, 2001) Assignee Kimberly-Clark Worldwide, Inc. 

A reactor was charged with 1-hydroxycyclohexyl phenyl ketone (0.05 mol), 100 ml THE, succinic anhydride (0.05 mol) and AICI3 (6.7 g). The mixture was stirred at 0°C 60 minutes, warmed to ambient temperature, and stirred 2 hours. Thereafter, the contents were 

The product from Step 1 (0.04 mol), 50 ml diethyl ether and thionyl chloride (0.05 mol) were mixed and stirred at 30°C 30 minutes. The solvent was removed at 0.01 Torr and the product isolated in 94% yield. 

A reactor was charged with 100 ml DMF, the product from Step 2 (98 mmol), /3-cyclodextrin (9.8 mmol) added, the mixture heated to 50°C, 0.5 ml TEA added, and the reaction continued one hour. Once at ambient temperature, the reaction volume was reduced by 90% by distillation and the remaining contents poured into iced brine solution. A precipitate formed and was isolated, dried, and powdered. It was purified using a 7.5 cm column containing 15 g silica gel using DMF. 

/8-Cyclodextrin-graft-4-(4-(hydroxylcyclohexylcarbonyl)phenyl) succinate-Malachite Green oxalate inclusion complex 

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The Nohr-McDonald elimination reaction is a high temperature tertiary alcohol dehydration performed using a high boiling point aromatic solvent with zinc chloride and is described by the author. A second transorber, (I), was prepared by the author using the Nohr-McDonald elimination reaction and subsequently used to prepare the /3-cyclodextrin graft polymer as illustrated in Eq. 1 ... 

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