2-Chlorophenol → 3-(Diethylamino)phenol

HRID 375670

Reaction equation

HRID 375670 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[NH2-].[Na+].[CH2:11]([NH:13][CH2:14][CH3:15])[CH3:12]>>[CH2:11]([N:13]([CH2:14][CH3:15])[C:7]1[CH:2]=[C:3]([OH:8])[CH:4]=[CH:5][CH:6]=1)[CH3:12]

Participants

4

Reactant 3

HCID 72452-ChlorophenolHCID 8021DiethylamineHCID 24533Sodium amide

Product 1

HCID 70623-(Diethylamino)phenolYield 76%

Procedure

32.1 g (0.25 mol) of o-chlorophenol were slowly added dropwise under nitrogen to a mixture of 20.5 g (0.5 mol) of 95% by weight pure crystalline sodium amide and 750 ml of diethylamine. The reaction mixture was refluxed under nitrogen for 72 h with stirring. The workup comprised hydrolysis with 100 ml of saturated aqueous ammonium chloride solution, distillative removal of excess diethylamine, neutralization with dilute hydrochloric acid up to a pH of 7.5, extraction of the residue with a total of 600 ml of methylene chloride, drying over sodium sulfate and concentrating of the organic phase. Thereafter the crude oil thus obtained (46.3 g) was distilled, which yielded 31.5 g (76%) of 3-diethylaminophenol (purity>96% (GC)).

Workup

  1. temperatureThe reaction mixture was refluxed under nitrogen for 72 h
  2. customhydrolysis
  3. customwith 100 ml of saturated aqueous ammonium chloride solution, distillative removal of excess diethylamine, neutralization with dilute hydrochloric acid
  4. extractionup to a pH of 7.5, extraction of the residue with a total of 600 ml of methylene chloride
  5. dry with materialdrying over sodium sulfate
  6. concentrationconcentrating of the organic phase
  7. customThereafter the crude oil thus obtained (46.3 g)
  8. distillationwas distilled

Sources & evidence

ORD record
ord-cc3170317df24e0da1d82fe75269e464
Source dataset
uspto-grants-1996_01
Patent number
US05486609

Linked notes

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