Acetone → 5-Chloro-2-(4-methoxyphenoxy)benzenamine

HRID 27623Notes

Reaction equation

HRID 27623 reaction equation
COC1C=CC([C:9]2[C:10]([N+]([O-])=O)=[C:11]([O:16][C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[C:19](C4C=CC(OC)=CC=4)[C:18]=3[N+:32]([O-])=O)[CH:12]=[CH:13][C:14]=2Cl)=CC=1.C[C:39](C)=[O:40].S(S([O-])=O)([O-])=O.[Na+].[Na+]>O>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]([O:16][C:11]2[CH:10]=[CH:9][C:14]([O:40][CH3:39])=[CH:13][CH:12]=2)=[C:18]([CH:19]=1)[NH2:32]

Participants

5

Reactant 3

HCID 180AcetoneHCID 24489Sodium DithioniteHCID 57238430HCID 57238430, compound

Product 1

HCID 24878325-Chloro-2-(4-methoxyphenoxy)benzenamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

An 80.0 g. portion of the above nitro derivative in 800 ml. of acetone is added to 320.0 g. of sodium hydrosulfite in 800 ml. of water. The mixture is heated to reflux on a steam bath for one hour, cooled and extracted with benzene. The benzene extract is washed with water, dried over anhydrous sodium sulfate, and evaporated in vacuo to a yellow oil. Treatment in hexane, with cooling produces crystals of 5-chloro-2-(p-methoxyphenoxy)-aniline.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux on a steam bath for one hour
  3. temperaturecooled
  4. extractionextracted with benzene
  5. extractionThe benzene extract
  6. washis washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customevaporated in vacuo to a yellow oil
  9. temperatureTreatment in hexane, with cooling

Sources & evidence

ORD record
ord-88a787f9ffe8471d837f061f01e8337d
Source dataset
uspto-grants-1980_09
Patent number
US04221714

Reaction notes

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