1-Butanol → N-Butyl-N-ethylaniline

HRID 1833985Notes

Reaction equation

HRID 1833985 reaction equation
[CH2:1]([NH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2].[CH2:10](O)[CH2:11][CH2:12][CH3:13].P(OC1C=CC=CC=1)(OC1C=CC=CC=1)OC1C=CC=CC=1>O>[CH2:1]([N:3]([CH2:10][CH2:11][CH2:12][CH3:13])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 2631-ButanolHCID 7540Triphenyl phosphiteHCID 7670N-Ethylaniline

Product 1

HCID 9989790N-Butyl-N-ethylanilineYield 69%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

182 parts of N-ethylaniline, 150 parts of n-butanol and 10 parts of triphenyl phosphite are heated for 20 hours at 230° C in a stirred autoclave. The autoclave is then let down and the water of reaction formed, unconverted ethylaniline and excess alcohol are distilled off. 183 parts of N-ethyl-N-butyl-aniline, corresponding to a yield of 69% of theory, distil at a boiling point of 88° - 91° C/5 mm Hg.

Workup

  1. customformed
  2. distillationunconverted ethylaniline and excess alcohol are distilled off
  3. custom183 parts of N-ethyl-N-butyl-aniline, corresponding to a yield of 69% of theory, distil at a boiling point of 88° - 91° C/5 mm Hg

Sources & evidence

ORD record
ord-38aa1074296d4a538115a4c3edadb121
Source dataset
uspto-grants-1978_01
Patent number
US04067903

Reaction notes

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