tert-Butanol → HCID 19013692, compound

Participants

Reaction Conditions

Reaction Steps

11.5 g (50 mmol) of the Diels-Alder reaction product of 3,3,3-trifluoro-2-trifluoromethyl-1-propene andcyclopentadiene are mixed in 10 ml of dry toluene with 326 mg (1 mmol) of molybdenum acetylacetonate, and 21 ml of a 2.9 molar solution of t-butyl hydroperoxide in toluene (61 mmol) is added dropwise at 22° C. within 30 minutes. During this period, the temperature rises to 45°C. The solution is then heated to 60° C., and after two and a half hours 3 g of molecular sieve 4 A and another 5 ml of the 2.9 molar solution of t-butyl hydroperoxide in toluene are added. After 20 hours of reaction time, the solvent, t-butanol and any remaining t-butyl hydroperoxide are carefully stripped off under reduced pressure. The residue is chromatographed on 160 g of silica gel. The mobile solvent usedis a mixture of hexane/methylene chloride/diethyl ether (10:10:0.5 parts byvolume). The product-containing fractions are combined and subjected to fractional distillation under reduced pressure. The product distils at a pressure of 150 to 190 mbar and a temperature of 100° to 124° C.

Provenance & Evidence