Phenol → 2-Nitro-5-phenoxytoluene

HRID 1371889

Reaction equation

HRID 1371889 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 27284182-Nitro-5-phenoxytoluene

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-cfe2c1da3b894920aeb02aa9e7e9f25a
Source dataset
uspto-grants-2007_01
Patent number
US07157488B2

Linked notes

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