2-(2,4-Bis(1,1-dimethylpropyl)phenoxy)butyryl chloride → 2-{2-(2,4-Di-t-amylphenoxy)butanamido}-4-chloro-5-nitrophenol

HRID 1904890Notes

Reaction equation

HRID 1904890 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[OH:12].[C:13]([C:18]1[CH:30]=[C:29]([C:31]([CH2:34][CH3:35])([CH3:33])[CH3:32])[CH:28]=[CH:27][C:19]=1[O:20][CH:21]([CH2:25][CH3:26])[C:22](Cl)=[O:23])([CH2:16][CH3:17])([CH3:15])[CH3:14]>C(OCC)(=O)C>[C:13]([C:18]1[CH:30]=[C:29]([C:31]([CH2:34][CH3:35])([CH3:32])[CH3:33])[CH:28]=[CH:27][C:19]=1[O:20][CH:21]([CH2:25][CH3:26])[C:22]([NH:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[OH:12])=[O:23])([CH2:16][CH3:17])([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 1703932-(2,4-Bis(1,1-dimethylpropyl)phenoxy)butyryl chlorideHCID 38948482-Amino-4-chloro-5-nitrophenol

Product 1

HCID 200361932-{2-(2,4-Di-t-amylphenoxy)butanamido}-4-chloro-5-nitrophenol

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

In 100 ml of ethyl acetate was dissolved 25 g (133×10-3 mole) of 2-amino-4-chloro-5-nitrophenol. To the solution was added 50 g of 2-(2,4-di-t-amylphenoxy)butanoic acid chloride at room temperature, and then the mixture was refluxed under heating for 2 hours. After the reaction, a solvent was evaporated under reduced pressure and the residue was recrystallized from hexane to obtain products. Yield: 61 g.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 2 hours
  3. customAfter the reaction
  4. customa solvent was evaporated under reduced pressure
  5. customthe residue was recrystallized from hexane
  6. customto obtain products

Sources & evidence

ORD record
ord-9ad603716cb442d58a78eca5095283e3
Source dataset
uspto-grants-1989_06
Patent number
US04840883

Reaction notes

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