1-Butanol → N-Butyl-m-toluidine

HRID 1833981Notes

Reaction equation

HRID 1833981 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[CH:3]=1.[CH2:9](O)[CH2:10][CH2:11][CH3:12].P(OC1C=CC=CC=1)(OC1C=CC=CC=1)OC1C=CC=CC=1>O>[CH2:9]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[CH:3]=1)[CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 2631-ButanolHCID 7540Triphenyl phosphiteHCID 7934m-Toluidine

Product 1

HCID 109036N-Butyl-m-toluidineYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

214 parts of m-toluidine, 75 parts of n-butanol and 10 parts of triphenyl phosphite are heated for 10 hours at 230° C in a stirred autoclave. The autoclave is then let down and the water of reaction formed, the excess of m-toluidine and the unconverted butanol are distilled off under reduced pressure. 130 parts of N-butyl-m-toluidine, corresponding to a yield of 80% of theory, distil at a boiling point of 65° - 70° C/0.2 mm Hg.

Workup

  1. customformed
  2. distillationthe excess of m-toluidine and the unconverted butanol are distilled off under reduced pressure
  3. custom130 parts of N-butyl-m-toluidine, corresponding to a yield of 80% of theory, distil at a boiling point of 65° - 70° C/0.2 mm Hg

Sources & evidence

ORD record
ord-6c40c5c7c1434c9fad0728dde80546bc
Source dataset
uspto-grants-1978_01
Patent number
US04067903

Reaction notes

Loading…