Diethyl Ether → Methyl rac-4,4-ethylenedioxy-1,2,3,4,5,12-hexahydro-2-hydroxy-5,12-dioxonaphthacene-2-carboxylate

HRID 1447489Notes

Reaction equation

HRID 1447489 reaction equation
C(O[C@@H:5]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C@H:6]1OC(=O)C)(=O)C.[CH2:17]1[CH2:37][O:36][C:19]2([C:28]3[C:27](=[O:29])[CH:26]=[CH:25][C:24](=[O:30])[C:23]=3[CH2:22][C:21]([OH:35])([C:31]([O:33][CH3:34])=[O:32])[CH2:20]2)[O:18]1.C(OCC)C>C1(C)C(C)=CC=CC=1>[CH2:37]1[CH2:17][O:18][C:19]2([C:28]3[C:27](=[O:29])[C:26]4[C:25](=[CH:6][C:7]5[C:8]([CH:5]=4)=[CH:9][CH:10]=[CH:11][CH:12]=5)[C:24](=[O:30])[C:23]=3[CH2:22][C:21]([OH:35])([C:31]([O:33][CH3:34])=[O:32])[CH2:20]2)[O:36]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 13264175trans-1,2-Diacetoxy-1,2-dihydrobenzocyclobuteneHCID 20283285Methyl rac-4,4-ethylenedioxy-1,2,3,4,5,8-hexahydro-2-hydroxy-5,8-dioxonaphthalene-2-carboxylate

Product 1

HCID 20283304Methyl rac-4,4-ethylenedioxy-1,2,3,4,5,12-hexahydro-2-hydroxy-5,12-dioxonaphthacene-2-carboxylateYield 74.6%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

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.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1.5 hours under an atmosphere of nitrogen
  3. customThe solution was evaporated
  4. customto give a bright yellow crystalline residue

Sources & evidence

ORD record
ord-60cb7033fc4a44d9b92079f5c99c4cd9
Source dataset
uspto-grants-1982_02
Patent number
US04316985

Reaction notes

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