Tetrahydrofuran → 2,5-dihydroxy benzoquinone copper (II)

HRID 1074379Notes

Reaction equation

HRID 1074379 reaction equation
[OH:1][C:2]1[C:3](=[O:10])[CH:4]=[C:5]([OH:9])[C:6](=[O:8])[CH:7]=1.O1CCCC1.C([O-])(=O)C.[Cu+2:20].C([O-])(=O)C>CN(C)C=O>[Cu+2:20].[OH:8][C:6]1[C:5](=[O:9])[CH:4]=[C:3]([OH:10])[C:2](=[O:1])[CH:7]=1

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran3×HCID 8895Cupric acetateHCID 692132,5-Dihydroxy-1,4-benzoquinone

Product 1

HCID 204963862,5-dihydroxy benzoquinone copper (II)

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

The 2,5-dihydroxy benzoquinone copper (II) polymer, (Table I, compound 5), Cu(DHBQ) is prepared as follows: Ten g of 2,5-dihydroxy benzoquinone are dissolved in 200 ml of either dimethylformamide (DMF) or tetrahydrofurane (THF). To this is added 14 g of copper acetate (hydrate) dissolved in 250 ml of DMF (or THF). The solution is refluxed for 4 hours. The products have to be centrifuged after being allowed to settle for a few days. The DMF solution yielded a brown product, and the THF yielded a blue product. Since the compounds were insoluble in all common solvents, purification and analysis was difficult. The only purification attempted was Soxhlet extraction using acetone as suggested by Coble and Holizclaw, J. Inorg, Nucl. Chem., 36,1049 (1974). The yield was about 10 g. The chain length is difficult to estimate, but low voltage mass spectral data (20 eV, CEC 450) show masses up to at least 600, indicating the molecule to be at least a trimer. The analytical data indicate copper=31.52% (found 30.2%); carbon=35.58% (found 37.88%; hydrogen=0.99% (found 2.39%. The IR spectra shows a carbonyl shift to 1470 cm-1 (from 1640 cm-1 in the starting DHBQ) and a loss of the phenolic absorption of 3300 cm-1. The fragmentation pattern from a high voltage (70 eV) mass spectral study is shown in Table III.

Workup

  1. temperatureThe solution is refluxed for 4 hours
  2. waitto settle for a few days
  3. customSince the compounds were insoluble in all common solvents, purification and analysis
  4. customThe only purification
  5. extractionSoxhlet extraction
  6. customa loss of the phenolic absorption of 3300 cm-1

Sources & evidence

ORD record
ord-a3ddc070b8ef4f738231da798e42224f
Source dataset
uspto-grants-1983_07
Patent number
US04391660

Reaction notes

Loading…