m-Chloroperbenzoic acid → Hexahydro-2H-3,5-methanocyclopenta[b]furan-6-ol

Temperature

0 °C

12.4 g of 5-hydroxy methyl-2-norbornene and 300 ml of methylene chloride were put in a flask, and 28.7 g (75% content) of m-chloro perbenzoic acid was dropped therein at 30° C. After completion of dropping, it was agitated at the temperature for 1 hour, then it was cooled to 0° C., and the precipitated benzoic acid was removed by filtration. The filtrate was washed with an aqueous solution of sodium sulfite, an aqueous solution of sodium bicarbonate, and then the organic layer was concentrated under a reduced pressure. The resultant crude 2,3-epoxy-5-hydroxy methyl norbornane, 100 ml of toluene and a catalytic amount of a concentrated sulfuric acid were put in a flask, and agitated at 50° C. for 2 hours. Then, usual after-treatment was carried out to yield 10.1 g of 2-hydroxy-4-oxatricyclo[4.2.1.03,7]nonane.

1. customat 30° C
2. customthe precipitated benzoic acid was removed by filtration
3. washThe filtrate was washed with an aqueous solution of sodium sulfite
4. concentrationan aqueous solution of sodium bicarbonate, and then the organic layer was concentrated under a reduced pressure
5. customThe resultant crude 2,3-epoxy-5-hydroxy methyl norbornane, 100 ml of toluene and a catalytic amount of a concentrated sulfuric acid were put in a flask
6. stirringagitated at 50° C. for 2 hours

ORD record

ord-283716c9f1934956ad170815c339ccae

Source dataset

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07169541B2