Benzyl Alcohol → N-Benzyl-4-methoxyaniline

HRID 1833980Notes

Reaction equation

HRID 1833980 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.[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>[CH2:10]([NH:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 7540Triphenyl phosphiteHCID 7732P-Anisidine

Product 1

HCID 519413N-Benzyl-4-methoxyanilineYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

369 parts of p-anisidine, 162 parts of benzyl alcohol and 15 parts of triphenyl phosphite are first heated to 177° C. At this temperature, the elimination of water commences. The condensation has ended after 5 hours, when the internal temperature is 231° C. 27 parts of water are removed. Excess p-anisidine and excess benzyl alcohol are distilled off under reduced pressure. 265 parts of N-benzyl-4-methoxy-aniline, corresponding to a yield of 83% of theory, distil at 190° C/5 mm Hg.

Workup

  1. customis 231° C
  2. custom27 parts of water are removed
  3. distillationExcess p-anisidine and excess benzyl alcohol are distilled off under reduced pressure
  4. custom265 parts of N-benzyl-4-methoxy-aniline, corresponding to a yield of 83% of theory, distil at 190° C/5 mm Hg

Sources & evidence

ORD record
ord-bede904dcaea4ab096ce933e0a926504
Source dataset
uspto-grants-1978_01
Patent number
US04067903

Reaction notes

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