Hydrogen Peroxide → 1a,2a,3,6,6a,7a-Hexahydro-3,6-methanonaphtho[2,3-b]oxirene-2,7-dione

Temperature

0 °C

A solution of tricyclo[6.2.1.02,7]undeca-4,9-diene-3,6-dione (14) (26.13 g, 150 mmol) in acetone (100 ml) was cooled to 0° C. on an ice-bath. To the solution was added saturated aqueous NaHCO3 (33 ml). To the mixture was added dropwise 34.5% aqueous hydrogen peroxide (142 ml) while keeping at 0° C. After the addition, the reaction mixture was stirred at 0° C. for 1 hr and then water (100 ml) was added. From the mixture solution, the product was extracted with diethyl ether (total 700 ml). The extract was washed with saturated aqueous NaCl and dried over magnesium sulfate, and the solvent was distilled off under reduced pressure to afford as the residue 4,5-epoxy-tricyclo[6.2.1.02,7]undec-9-ene-3,6-dione (15) (28.06 g, 148 mmol, 98.35% yield) in light ID yellowish white crystals.

1. customwhile keeping at 0° C
2. additionAfter the addition
3. extractionFrom the mixture solution, the product was extracted with diethyl ether (total 700 ml)
4. washThe extract was washed with saturated aqueous NaCl
5. dry with materialdried over magnesium sulfate
6. distillationthe solvent was distilled off under reduced pressure

ORD record

ord-11c956355b7c4491b825bd3bff4e8c62

Source dataset

uspto-grants-2003_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06642424B2