4-Nitrophenol → HCID 57000381, compound

HRID 2418312Notes

Reaction equation

HRID 2418312 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7](O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH:11]([O:13][C:14](=O)[CH3:15])=[CH2:12]>>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:12]=[CH:11][O:13][CH:14]=[CH:15][C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 9804-NitrophenolHCID 7904Vinyl Acetate

Product 1

HCID 57000381HCID 57000381, compoundYield 55.5%

Conditions

Temperature
50 °C

Procedure

104 g (0.75 Mol) of 4-nitrophenol are dissolved in 420 ml (4.5 Mol) acetic acid vinyl ester. After washing with nitrogen, successively 3.0 g mercury acetate and 0.2 ml BF3 -etherate are added. The reaction mixture is stirred for 4 hours at 50° C. After cooling, 2 g sodium acetate are added, evaporated, and the residue then dissolved in ether. There follows washing three times with 2 n-caustic soda, three times with water, drying and evaporation. The residue is recrystallized from ether. 65 g (52% of theoretical amount) of 4-nitrophenylvinylether are obtained, with a melting point of 59°-61° C.

Workup

  1. washAfter washing with nitrogen, successively 3.0 g mercury acetate and 0.2 ml BF3 -etherate
  2. additionare added
  3. temperatureAfter cooling
  4. addition2 g sodium acetate are added
  5. customevaporated
  6. dissolutionthe residue then dissolved in ether
  7. washThere follows washing three times with 2 n-caustic soda, three times with water
  8. customdrying
  9. customevaporation
  10. customThe residue is recrystallized from ether

Sources & evidence

ORD record
ord-bc9bf44091d249998d1214e4eda6877b
Source dataset
uspto-grants-1984_09
Patent number
US04472434

Reaction notes

Loading…