Water → HCID 22352092, compound

HRID 896729Notes

Reaction equation

HRID 896729 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1F)([O-:3])=[O:2].[CH:14]([C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)=[CH2:15].C([O-])([O-])=O.[K+].[K+].O>CN1C(=O)CCC1>[CH:14]([C:16]1[CH:21]=[CH:20][C:19]([O:22][C:5]2[CH:6]=[CH:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])=[CH:18][CH:17]=1)=[CH2:15]

Participants

6

Reactant 4

HCID 962WaterHCID 6264DinitrofluorobenzeneHCID 11430Potassium CarbonateHCID 624534-Vinylphenol

Product 1

HCID 22352092HCID 22352092, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 2,4-dinitrofluorobenzene (6.38 g, 34 mmol), 4-vinylphenol (4.32 g, 36 mmol), 4.97 g K2CO3 and 2-3 crystals of BHT inhibitor was dissolved in 75 ml NMP and stirred at 40° C. under nitrogen for 4 hr. The reaction mixture was poured into a separatory funnel containing 150 ml water and extracted 3×100 mls with ethyl acetate. The combined organics were washed with 100 ml 10% KOH, and brine, dried with anhydrous MgSO4 and concentrated. The residue was recrystallized from 70% ethyl acetate in hexane yielding 9.5 g product.

Workup

  1. additionThe reaction mixture was poured into a separatory funnel
  2. extractionextracted 3×100 mls with ethyl acetate
  3. washThe combined organics were washed with 100 ml 10% KOH, and brine
  4. dry with materialdried with anhydrous MgSO4
  5. concentrationconcentrated
  6. customThe residue was recrystallized from 70% ethyl acetate in hexane yielding 9.5 g product

Sources & evidence

ORD record
ord-cc8e073ee11048c7badc5ce7ac3851a7
Source dataset
uspto-grants-2005_07
Patent number
US06919404B2

Reaction notes

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