Sulfuric Acid → Allyl 3-(1-adamantyl)-2-fluoro-4hydroxybenzoate

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Reaction Steps

In a 250 ml three-necked flask, under nitrogen, one introduces 3.04 g 1-adamantanol, 10 ml of n-heptane and 63 μl concentrated sulfuric acid. Dropwise, 2.16 ml of acetic anhydride are added and stirring is conducted for 3 hours at room temperature. Dropwise, 540 μl concentrated sulfuric acid are added and one adds portionwise 3.92 g of allyl 2-fluoro-4-hydroxybenzoate. After this addition, one adds 25 ml of dichloromethane and agitates at room temperature for 24 hours. After vacuum drying, the solid is taken up in water, neutralized to pH 7 with sodium bicarbonate and extracted with ethyl ether. The organic layer is washed with water and then with a concentrated aqueous sodium chloride solution. After drying over magnesium sulfate, one filters and evaporates the filtrate to obtain 7 g of crude product which is chromatographed on a silica column and eluted with dichloromethane. After trituration with hexane, filtration and drying in an oven at 50° C. there were obtained 3.86 g of the desired product, melting at 219°-222° C.

Provenance & Evidence