Benzyl Alcohol → N-Ethyl-N-benzylaniline
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)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.P(OC1C=CC=CC=1)(OC1C=CC=CC=1)OC1C=CC=CC=1>O>[CH2:1]([N:3]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 210 °C
Procedure
182 parts of N-ethylaniline, 170 parts of benzyl alcohol and 10 parts of triphenyl phosphite are mixed whilst stirring and next heated to an internal temperature of 184° C, at which the elimination of water commences. The mixture is then heated to an internal temperature of 210° C in the course of 8 hours. During this time, 25 parts of water have distilled off and the condensation has ended. The excess ethylaniline and unconverted benzyl alcohol are then distilled off. 276 parts of N-ethyl-N-benzyl-aniline, corresponding to a yield of 87% of theory, distil at a boiling point of 140° - 144° C/5 mm Hg.
Workup
- distillationDuring this time, 25 parts of water have distilled off
- distillationThe excess ethylaniline and unconverted benzyl alcohol are then distilled off
- custom276 parts of N-ethyl-N-benzyl-aniline, corresponding to a yield of 87% of theory, distil at a boiling point of 140° - 144° C/5 mm Hg
Sources & evidence
- ORD record
- ord-ec2e902f710946a0bd52fce0ec8f0ad4
- Source dataset
- uspto-grants-1978_01
- Patent number
- US04067903
Reaction notes
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