trans-1,2-Diacetoxy-1,2-dihydrobenzocyclobutene → Methyl rac-1,2,3,4,5,12-hexahydro-5,12-dioxonaphthacene-2-carboxylate

HRID 463473Notes

Reaction equation

HRID 463473 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.[O:17]=[C:18]1[CH:27]=[CH:26][C:25](=[O:28])[C:24]2[CH2:23][CH:22]([C:29]([O:31][CH3:32])=[O:30])[CH2:21][CH2:20][C:19]1=2>C1(C)C(C)=CC=CC=1>[O:17]=[C:18]1[C:27]2[C:26](=[CH:6][C:7]3[C:8]([CH:5]=2)=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:25](=[O:28])[C:24]2[CH2:23][CH:22]([C:29]([O:31][CH3:32])=[O:30])[CH2:21][CH2:20][C:19]1=2

Participants

4

Reactant 2

HCID 13264175trans-1,2-Diacetoxy-1,2-dihydrobenzocyclobuteneHCID 20283297Methyl rac-1,2,3,4,5,8-hexahydro-5,8-dioxonaphthalene-2-carboxylate

Product 1

HCID 20283275Methyl rac-1,2,3,4,5,12-hexahydro-5,12-dioxonaphthacene-2-carboxylateYield 81.2%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 240 mg (1.1 mmol) of trans-1,2-diacetoxy-1,2-dihydrobenzocyclobutene and 220 mg (1.0 mmol) of methyl rac-1,2,3,4,5,8-hexahydro-5,8-dioxonaphthalene-2-carboxylate in 20 ml of dry xylene was stirred and heated under reflux under an atmosphere of nitrogen for 18 hours. The solution was evaporated to dryness, the yellow residue was stirred with 10 ml of diethyl ether and the mixture was subsequently filtered to give 260 mg (81%) of methyl rac-1,2,3,4,5,12-hexahydro-5,12-dioxonaphthacene-2-carboxylate in the form of a bright yellow solid of melting point 173°-174° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux under an atmosphere of nitrogen for 18 hours
  3. customThe solution was evaporated to dryness
  4. stirringthe yellow residue was stirred with 10 ml of diethyl ether
  5. filtrationthe mixture was subsequently filtered

Sources & evidence

ORD record
ord-cd0c6956a1194751859415a76523431e
Source dataset
uspto-grants-1985_05
Patent number
US04518784

Reaction notes

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