tert-Butanol → HCID 19013692, compound

Temperature

60 °C

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.

1. additionis added dropwise at 22° C. within 30 minutes
2. waitDuring this period
3. customrises to 45°C
4. waitafter two and a half hours 3 g of molecular sieve 4 A
5. customAfter 20 hours of reaction time
6. customThe residue is chromatographed on 160 g of silica gel
7. additionThe mobile solvent usedis a mixture of hexane/methylene chloride/diethyl ether (10:10:0.5 parts byvolume)
8. distillationsubjected to fractional distillation under reduced pressure
9. customThe product distils at a pressure of 150 to 190 mbar
10. customa temperature of 100° to 124° C.

ORD record

ord-87b38896b5754d99808ea4dfdc98688d

Source dataset

uspto-grants-1994_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05331084