Phenol → 2-(Dimethoxymethyl)-1-nitro-4-phenoxybenzene

HRID 1968772

Reaktionsgleichung

Reaktionsgleichung von HRID 1968772
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([CH:11]([O:14][CH3:15])[O:12][CH3:13])[CH:3]=1.[C:16]1([OH:22])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].C(OC(C)C)(C)C>CC(N(C)C)=O.C(Cl)Cl.O>[CH3:13][O:12][CH:11]([O:14][CH3:15])[C:4]1[CH:3]=[C:2]([O:22][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:7]=[CH:6][C:5]=1[N+:8]([O-:10])=[O:9]

Komponenten

8

Edukt 4

HCID 996PhenolHCID 7914Diisopropyl EtherHCID 11430Potassium CarbonateHCID 35700934-Chloro-2-(dimethoxymethyl)-1-nitrobenzene

Produkt 1

HCID 34804522-(Dimethoxymethyl)-1-nitro-4-phenoxybenzene

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A mixture of 4-chloro-2-dimethoxymethyl-1-nitrobenzene (11.55 g, 0.0500 mol), phenol (4.70 g, 0.0500 mol), and potassium carbonate (8.16 g, 0.0600 mol) in DMA (100 mL) was stirred at 150° C. for 6 h. After cooling, the reaction mixture was poured into water and treated with diisopropyl ether. The organic layer was separated, washed with 10% aqueous KOH solution, dried (MgSO4), filtered, and concentrated. The resulting residue was purified by column chromatography on silica gel using as eluent CH2Cl2:petroleum ether (40:60, 60:40,100:0 gradient). The product containing fractions were combined and evaporated to yield a residue which was dissolved in CH2Cl2 and washed with 10% aqueous KOH solution to remove the remaining phenol. Drying and evaporation yielded a residue.

Aufarbeitung

  1. temperatureAfter cooling
  2. customThe organic layer was separated
  3. washwashed with 10% aqueous KOH solution
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was purified by column chromatography on silica gel using as eluent CH2Cl2:petroleum ether (40:60, 60:40,100:0 gradient)
  8. additionThe product containing fractions
  9. customevaporated
  10. customto yield a residue which
  11. washwashed with 10% aqueous KOH solution
  12. customto remove the remaining phenol
  13. customDrying
  14. customevaporation
  15. customyielded a residue

Quellen und Nachweise

ORD-Eintrag
ord-03c1294a50ad4b1f9b3c9f578c51a0e2
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08426429B2

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