Réaction #549808

Équation de réaction

trans-1,2-diacetoxy-1,2-dihydrobenzocyclobutene

methyl rac-4,4-ethylenedioxy-1,2,3,4,5,8-hexahydro-2-hydroxy-5,8-dioxonaphthalene-2-carboxylate

diethyl ether

→

methyl rac-4,4-ethylenedioxy-1,2,3,4,5,12-hexahydro-2-hydroxy-5,12-dioxonaphthacene-2-carboxylate

Rendement 74.6%

Solvants

xylene

Conditions de réaction

Traitement

1. 1
   Températureheated
2. 2
   Températureunder reflux for 1.5 hours under an atmosphere of nitrogen
3. 3
   AutreThe solution was evaporated
4. 4
   Autreto give a bright yellow crystalline residue

Mode opératoire

A solution of 200 mg of trans-1,2-diacetoxy-1,2-dihydrobenzocyclobutene and 100 mg of methyl rac-4,4-ethylenedioxy-1,2,3,4,5,8-hexahydro-2-hydroxy-5,8-dioxonaphthalene-2-carboxylate in 10 ml of xylene was stirred and heated under reflux for 1.5 hours under an atmosphere of nitrogen. The solution was evaporated to give a bright yellow crystalline residue. Trituration of this residue with diethyl ether gave 100 mg (74.5%) of methyl rac-4,4-ethylenedioxy-1,2,3,4,5,12-hexahydro-2-hydroxy-5,12-dioxonaphthacene-2-carboxylate in the form of yellow crystals of melting point 207°-209° C.

Source