Potassium Carbonate → 3,4-Bis(2,2,2-trifluoroethoxy)nitrobenzene

HRID 262740Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 262740
[C:1](=[O:4])([O-])[O-].[K+].[K+].FC(F)(F)S([O:12][CH2:13][C:14]([F:17])([F:16])[F:15])(=O)=O.[N+:20]([C:23]1[CH:24]=[C:25](O)[C:26](=[CH:28][CH:29]=1)O)([O-:22])=[O:21]>CC(C)=O>[F:17][C:14]([F:15])([F:16])[CH2:13][O:12][C:28]1[CH:29]=[C:23]([N+:20]([O-:22])=[O:21])[CH:24]=[CH:25][C:26]=1[O:4][CH2:1][C:14]([F:17])([F:16])[F:15]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 35051094-Nitrocatechol

Produkt 1

HCID 133704333,4-Bis(2,2,2-trifluoroethoxy)nitrobenzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel2×

Versuchsvorschrift

To a refluxing mixture of 12.7 g. (0.092 mole) of potassium carbonate, 21.3 g. (0.092 mole) of 2,2,2-trifluoroethyl trifluoromethanesulfonate and 62 ml. of acetone is added dropwise 6.2 g. (0.040 mole) of 4-nitrocatechol in 62 ml. of acetone over about 2.5 hours. Refluxing is continued for a total of 24 hours, then the solution is evaporated. The residue is mixed with equal volumes of water and diethyl ether. The ether layer is separated, washed with water and saturated sodium chloride solution and dried. Evaporation provides crude 3,4-bis(2,2,2-trifluoroethoxy)nitrobenzene. Chromatographic purification on a silica gel column is effected by eluting with mixtures of chloroform and hexane. Recrystallization from cyclohexane with a small amount of benzene provides solid product, m.p. 63°-65° C.

Aufarbeitung

  1. additionTo a refluxing mixture of 12.7 g
  2. temperatureRefluxing
  3. customis continued for a total of 24 hours
  4. customthe solution is evaporated
  5. additionThe residue is mixed with equal volumes of water and diethyl ether
  6. customThe ether layer is separated
  7. washwashed with water and saturated sodium chloride solution
  8. customdried
  9. customEvaporation

Quellen und Nachweise

ORD-Eintrag
ord-212aba99a9fb43f4bbf7b4c6ede818b9
Quelldatensatz
uspto-grants-1979_05
Patentnummer
US04154941

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