2,4-Dichloro-6-nitrophenol → HCID 68122147, compound

HRID 437610Notes

Reaction equation

HRID 437610 reaction equation
[C:1](Cl)(=[O:5])/[CH:2]=[CH:3]/[CH3:4].[Cl:7][C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[C:10]([N+:15]([O-:17])=[O:16])[C:9]=1[OH:18]>C(Cl)Cl>[C:1]([O:18][C:9]1[C:10]([N+:15]([O-:17])=[O:16])=[CH:11][C:12]([Cl:14])=[CH:13][C:8]=1[Cl:7])(=[O:5])/[CH:2]=[CH:3]/[CH3:4]

Participants

4

Reactant 2

HCID 118712,4-Dichloro-6-nitrophenolHCID 643131trans-Crotonyl chloride

Product 1

HCID 68122147HCID 68122147, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Crotonyl chloride (7 ml) was added to a solution of 2,4-dichloro-6-nitrophenol (10.3 g) in methylene chloride (20 ml) and the mixture was heated under reflux for 12 hours. The solution was diluted with further methylene chloride (200 ml) and extracted several times with a 10% sodium hydroxide solution. The organic layer was washed with water dried (Na2SO4) and the solvent removed under reduced pressure to give a pale brown oil which crystallised on standing for 24 hours 2,4-dichloro-6-nitrophenyl crotonate melted at <60°.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 12 hours
  3. extractionextracted several times with a 10% sodium hydroxide solution
  4. washThe organic layer was washed with water
  5. dry with materialdried (Na2SO4)
  6. customthe solvent removed under reduced pressure
  7. customto give a pale brown oil which
  8. customcrystallised

Sources & evidence

ORD record
ord-054609431cda4882a1a5d0fc4bcd9d80
Source dataset
uspto-grants-1977_06
Patent number
US04031249

Reaction notes

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