Phosphorus oxychloride → HCID 13827097, compound

HRID 1252714Notes

Reaction equation

HRID 1252714 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[C:6]([CH2:13][CH3:14])[C:5]=1O)([O-:3])=[O:2].P(Cl)(Cl)([Cl:18])=O>>[Cl:18][C:5]1[C:6]([CH2:13][CH3:14])=[CH:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1232072-Ethyl-4,6-dinitrophenol

Product 1

HCID 13827097HCID 13827097, compound

Procedure

2,4-Dinitro-6-ethylphenol (10 g) was placed in a 250 ml round bottom flask, and phosphorous oxychloride (60 ml, Fisher) was added. N,N-diethylamiline (15 ml, Aldrich) was added portionwise, and the mixture became hot. The flask was placed under a condenser equiped with a drying tube heated on a steam bath for two hours and cooled. The mixture was then carefully poured onto ice, with stirring and extracted with ethyl acetate. The ethyl acetate layer was washed with brine, dried over MgSO4 and evaporated to a dark oil which was columned on silica gel using 10% ethyl acetate petroleum ether. The evaporated filtrates gave a reddish oil, which solidified upon being pumped dry. The solid was recrystallized from ethyl acetate-petroleum ether to give pale yellow needles of 1-chloro-2,4-dinitro-6-ethylbenzene.

Workup

  1. additionN,N-diethylamiline (15 ml, Aldrich) was added portionwise
  2. customThe flask was placed under a condenser
  3. customequiped with a drying tube
  4. temperatureheated on a steam bath for two hours
  5. temperaturecooled
  6. additionThe mixture was then carefully poured onto ice
  7. extractionextracted with ethyl acetate
  8. washThe ethyl acetate layer was washed with brine
  9. dry with materialdried over MgSO4
  10. customevaporated to a dark oil which
  11. customThe evaporated filtrates gave a reddish oil, which
  12. customupon being pumped dry
  13. customThe solid was recrystallized from ethyl acetate-petroleum ether

Sources & evidence

ORD record
ord-34c4cb52e86a4fd8a455accaca93ee88
Source dataset
uspto-grants-1988_05
Patent number
US04745116

Reaction notes

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