2-Nitrophenol → HCID 54051739, compound

HRID 1395112Notes

Reaction equation

HRID 1395112 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])([O-:3])=[O:2].[CH2:11](Br)[CH:12]=[CH2:13].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH:11]([O:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])=[CH:12][CH3:13]

Participants

5

Reactant 3

HCID 69472-NitrophenolHCID 7841Allyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 54051739HCID 54051739, compoundYield 91.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Nitrophenol (142.0 g, 1.02 mole), allyl bromide (120.9 g, 1.00 mole), anhydrous potassium carbonate (140.0 g, 1.02 mole) and dry acetone (500 cc) were refluxed for 21 hours, and filtered to remove the potassium bromide. The residue was washed with acetone and the solvent was removed by rotary evaporation. The residue was partitioned between 200 cc of dichloromethane and water. The dichloromethane layer was washed with 200 cc of 10% potassium hydroxide, separated and the solvent was removed by rotary evaporation. The crude product was fractionally distilled at 124° C. at 2.0 mm. Hg to yield 164.7 g of product (91.9%).

Workup

  1. filtrationfiltered
  2. customto remove the potassium bromide
  3. washThe residue was washed with acetone
  4. customthe solvent was removed by rotary evaporation
  5. customThe residue was partitioned between 200 cc of dichloromethane and water
  6. washThe dichloromethane layer was washed with 200 cc of 10% potassium hydroxide
  7. customseparated
  8. customthe solvent was removed by rotary evaporation
  9. distillationThe crude product was fractionally distilled at 124° C. at 2.0 mm. Hg

Sources & evidence

ORD record
ord-c1a90aa73a9c491b9ac5615ac7f10649
Source dataset
uspto-grants-1980_05
Patent number
US04202821

Reaction notes

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