Methane → 3-Acetoacetoxyadamantan-1-yl methacrylate

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3-(Acetoacetyloxy)adamantyl methacrylate (AAHAMA) was prepared according to the following procedure. 65.6 g of 3-hydroxyadamantan-1-yl methacrylate (HAMA) (277.6 mmol) and 42.1 g of 95% pure 2,2,6-trimethyl-4H-1,3-dioxin-4-one (277.6 mmol) were mixed with 0.2 g of CYANOX® 1790 inhibitor in 400 ml of toluene. After refluxing (110° C.) for 4 hours, the reaction was cooled, 10 g of activated charcoal and 400 ml of toluene were added, and the mixture stirred overnight. After filtration, another 10 g of activated charcoal was added, and the mixture stirred for an additional 12 h., then filtered. The filtrate was concentrated and run through a silica gel flash column with ethyl acetate as eluant. The solvent was then removed to yield 80 g (90%) of 3-acetoacetoxyadamantan-1-yl methacrylate was obtained.

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