Hydroquinone → HCID 23046828, compound

Temperature

20 °C

244 ml of cyclopentadiene were slowly added to a mixture of 208 g of 5-hydroxy-2(5H)-furanone, 350 mg of hydroquinone and 1.05 liters of chloroform while keeping the temperature at 45°-47° C. and the mixture was stirred at 20° C. for 17 hours and was evaporated to dryness under reduced pressure. The residue was added to isopropyl ether and the mixture was heated to reflux with stirring and was cooled and vacuum filtered. The solid was dissolved in methylene chloride and the solution was treated with activated carbon and evaporated to dryness under reduced pressure. The residue and isopropyl ether was heated to reflux with stirring and was cooled and vacuum filtered to obtain 325.7 g of racemic 1-hydroxy-3-oxo-1,3,3a,7a-tetrahydro-4,7-methano-isobenzofuran melting at 105° C.

1. customat 45°-47° C.
2. customwas evaporated to dryness under reduced pressure
3. additionThe residue was added to isopropyl ether
4. temperaturethe mixture was heated
5. temperatureto reflux
6. stirringwith stirring
7. temperaturewas cooled
8. filtrationvacuum filtered
9. dissolutionThe solid was dissolved in methylene chloride
10. additionthe solution was treated with activated carbon
11. customevaporated to dryness under reduced pressure
12. temperatureThe residue and isopropyl ether was heated
13. temperatureto reflux
14. stirringwith stirring
15. temperaturewas cooled
16. filtrationvacuum filtered

ORD record

ord-5203754b68f04194ba5cf2c375ece235

Source dataset

uspto-grants-1990_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04935532