2-(Chloromethyl)-4-nitrophenol → HCID 22749431, compound

HRID 2163797Notes

Reaction equation

HRID 2163797 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11].C([O-])(=O)C.[Na+].[OH:17][C:18]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][C:19]=1[CH2:20]Cl>>[OH:11][C:3]1[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[NH:1][CH2:20][C:19]1[CH:22]=[C:23]([N+:26]([O-:28])=[O:27])[CH:24]=[CH:25][C:18]=1[OH:17]

Participants

4

Reactant 3

HCID 763052-(Chloromethyl)-4-nitrophenolHCID 517045Sodium AcetateHCID 36133892-Amino-4-Nitrophenol

Product 1

HCID 22749431HCID 22749431, compound

Procedure

15.4 g. of 2-amino-4-nitrophenol and 8.2 g. of sodium acetate were added to 200 ml. of an alcohol and the mixture was heated under reflux. To the mixture was added dropwise 19.6 g. of 2-hydroxy-5-nitrobenzyl chloride dissolved in 70 ml. of an alcohol over a period of time of 30 minutes. After the reaction was effected for about 2 hours, the alcohol was distilled off. The reaction mixture was extracted with ethyl acetate and the extract was washed with water and concentrated by distilling off the ethyl acetate to have crystals precipitated. The crystals were recrystallized from 250 ml. of acetonitrile to obtain the end product. The melting point of the end product was 170°-220° C. (decomp.) and the yield was 24 g.

Workup

  1. temperatureunder reflux
  2. additionTo the mixture was added dropwise 19.6 g
  3. distillationthe alcohol was distilled off
  4. extractionThe reaction mixture was extracted with ethyl acetate
  5. washthe extract was washed with water
  6. concentrationconcentrated
  7. distillationby distilling off the ethyl acetate
  8. customprecipitated
  9. customThe crystals were recrystallized from 250 ml
  10. customof acetonitrile to obtain the end product

Sources & evidence

ORD record
ord-927b8b0ad1d64c7ea3d1a4371e980c42
Source dataset
uspto-grants-1979_01
Patent number
US04137080

Reaction notes

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