4-Iodo-1,2-dimethoxybenzene → 4-Phenoxycatechol dimethyl ether

HRID 1111682

Reaktionsgleichung

Reaktionsgleichung von HRID 1111682
I[C:2]1[CH:3]=[C:4]([O:10][CH3:11])[C:5]([O:8][CH3:9])=[CH:6][CH:7]=1.[O-:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Na+]>[Cu]>[CH3:9][O:8][C:5]1[C:4](=[CH:3][C:2]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[O:10][CH3:11]

Komponenten

4

Edukt 2

HCID 2303074-Iodo-1,2-dimethoxybenzeneHCID 4445035Phenolate Sodium

Produkt 1

HCID 113792174-Phenoxycatechol dimethyl ether

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23978CopperKatalysator

Versuchsvorschrift

R = 4-phenoxy. Heating a mixture of 4-iodoveratrol (Janssen et al., J. Org. Chem. 20, 1326 (1955)), sodium phenoxide and a catalytic amount of copper powder at about 200° C. for about 4 hours, then pouring the mixture over ice, extracting the mixture with an organic solvent such as ether, drying the extract, stripping the solvent and distilling the residue to give 4-phenoxycatechol dimethyl ether. Treating this product with an anhydrous aluminum chloride/sodium chloride melt (Janssen et al., supra), pouring the resulting mixture into ice-hydrochloric acid, extracting the mixture with an organic solvent, stripping the solvent under reduced pressure and fractionally distilling the residue gives the desired 4-phenoxycatechol.

Aufarbeitung

  1. temperatureHeating
  2. additionpouring the mixture over ice
  3. extractionextracting the mixture with an organic solvent such as ether
  4. customdrying the extract
  5. distillationdistilling the residue

Quellen und Nachweise

ORD-Eintrag
ord-1fd62c14731248899ee72535d88a4184
Quelldatensatz
uspto-grants-1978_10
Patentnummer
US04118507

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