2-Phenylethanol → 4-Methoxy-N-(2-phenylethyl)aniline

HRID 1833977Notes

Reaction equation

HRID 1833977 reaction equation
[C:1]1([CH2:7][CH2:8]O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=1.P(OC1C=CC=CC=1)(OC1C=CC=CC=1)OC1C=CC=CC=1>O>[C:1]1([CH2:7][CH2:8][NH:18][C:15]2[CH:16]=[CH:17][C:12]([O:11][CH3:10])=[CH:13][CH:14]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 60542-PhenylethanolHCID 7540Triphenyl phosphiteHCID 7732P-Anisidine

Product 1

HCID 127099124-Methoxy-N-(2-phenylethyl)anilineYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent4×

Conditions

Temperature
250 °C

Procedure

244 parts of phenylethyl alcohol, 450 parts of p-anisidine and 30 parts of triphenyl phosphite are mixed and heated, using a water separator, initially to 210° C, at which temperature the elimination of water commences. The internal temperature is raised to 250° C in the course of 8 hours. After this time, the elimination of water has ended (36 parts of water). The mixture is worked up by distillation under reduced pressure. After distilling off excess alcohol and amine, the N-(2'-phenylethyl)-4-methoxy-aniline distils at a boiling point of 187° - 190° C/5 mm Hg. 372 parts of N-(2'-phenylethyl)-4-methoxyaniline (89% of theory) are obtained.

Workup

  1. temperatureheated
  2. custominitially to 210° C
  3. distillationThe mixture is worked up by distillation under reduced pressure
  4. distillationAfter distilling off excess alcohol and amine
  5. customthe N-(2'-phenylethyl)-4-methoxy-aniline distils at a boiling point of 187° - 190° C/5 mm Hg

Sources & evidence

ORD record
ord-902a4574a62746e99246c43aa2eb24c8
Source dataset
uspto-grants-1978_01
Patent number
US04067903

Reaction notes

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