Phenol → 2-Nitro-5-phenoxytoluene

HRID 1666829

Reaktionsgleichung

Reaktionsgleichung von HRID 1666829
[OH-].[K+].[C:3]1([OH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.F[C:11]1[CH:12]=[CH:13][C:14]([N+:18]([O-:20])=[O:19])=[C:15]([CH3:17])[CH:16]=1>[OH-].[Na+]>[N+:18]([C:14]1[CH:13]=[CH:12][C:11]([O:9][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)=[CH:16][C:15]=1[CH3:17])([O-:20])=[O:19]

Komponenten

5

Edukt 3

HCID 996PhenolHCID 14797Potassium Hydroxide2×HCID 949565-Fluoro-2-nitrotoluene

Produkt 1

HCID 27284182-Nitro-5-phenoxytoluene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

Combine potassium hydroxide (3 g, 0.054 mol) and phenol (15 g, 0.16 mol), and heat to 110° C. until the potassium hydroxide is dissolved. Cool the mixture to room temperature and add 5-fluoro-2-nitrotoluene (7.75 g, 0.05 mol) in one aliquot. Heat the reaction mixture to 130° C. for 30 min, cool to room temperature, and then pour into 10% NaOH (200 mL). Extract the aqueous solution with ether (2×100 mL), combine the organic layers and wash with 10% NaOH (2×100 mL), water (2×100 mL), dry over Na2SO4 and concentrate in vacuo. Chromatograph on silica gel eluting with hexanes/ethyl acetate to give 2-nitro-5-phenoxytoluene as a solid: 1H NMR (300 MHz, CDCl3) 2.59 (s, 3H), 6.81-6.85 (m, 2H), 7.06-7.09 (m, 2H), 7.22-7.26 (m, 1H), 7.40-7.45 (m, 2H), 8.03-8.06 (m, 1H).

Aufarbeitung

  1. dissolutionis dissolved
  2. temperatureHeat the reaction mixture to 130° C. for 30 min
  3. temperaturecool to room temperature
  4. extractionExtract the aqueous solution with ether (2×100 mL)
  5. washwash with 10% NaOH (2×100 mL), water (2×100 mL)
  6. dry with materialdry over Na2SO4
  7. concentrationconcentrate in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-401c4b12c1fe4aa696f806c9953f7f27
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044090B2

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