4-Tert-octylphenol → HCID 22471698, compound

HRID 1004648Notes

Reaction equation

HRID 1004648 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[C:17]([C:25]1[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=1)([CH2:20][C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:19])[CH3:18]>CN(C)C=O.O>[CH3:19][C:17]([C:25]1[CH:26]=[CH:27][C:28]([O:31][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)=[CH:29][CH:30]=1)([CH3:18])[CH2:20][C:21]([CH3:22])([CH3:23])[CH3:24]

Participants

6

Reactant 3

HCID 88144-Tert-octylphenolHCID 9590p-FluoronitrobenzeneHCID 11430Potassium Carbonate

Product 1

HCID 22471698HCID 22471698, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 1-fluoro-4-nitrobenzene (3.4 g, 0.024 mol), K2CO3 (6.6 g, 48 mmol) and 4-(tert-octyl)phenol (5.0 g, 0.024 mol) in dimethylformamide (50 mL) was heated at reflux for 24 hours. The mixture was allowed to cooled to room temperature, diluted with water (200 mL), and extracted with ethyl acetate (250 mL). The organic phase was washed with water (5×100 mL), dried (Na2SO4), and concentrated under reduced pressure to afford the desired product as a yellow solid (7.8 g, 100%): 1H NMR (DMSO-d6, 300 MHz) δ 8.24 (d, 9.2 Hz, 2 H), 7.48 (d, 8.8 Hz, 2 H), 7.09-7.05 (m, 4H), 1.72 (s, 2 H), 1.34 (s, 6 H), 0.69 (s, 9 H); MS (FAB) m/z 328 (MH+); Rf =0.92 (15:85 ethyl acetate/hexane).

Workup

  1. temperatureat reflux for 24 hours
  2. extractionextracted with ethyl acetate (250 mL)
  3. washThe organic phase was washed with water (5×100 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4b78a5cb3a434ff4b091cbd0e4830999
Source dataset
uspto-grants-2000_04
Patent number
US06051586

Reaction notes

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