2-Phenylethanol → 3-Methyl-N-(2-phenylethyl)aniline

HRID 1833976Notes

Reaction equation

HRID 1833976 reaction equation
[C:1]1([CH2:7][CH2:8]O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[CH:12]=1.P(OC1C=CC=CC=1)(OC1C=CC=CC=1)OC1C=CC=CC=1>O>[C:1]1([CH2:7][CH2:8][NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 60542-PhenylethanolHCID 7540Triphenyl phosphiteHCID 7934m-Toluidine

Product 1

HCID 126647693-Methyl-N-(2-phenylethyl)anilineYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent4×

Conditions

Temperature
236 °C

Procedure

260 parts of phenylethyl alcohol, 428 parts of m-toluidine and 20 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 236° C in the course of 8 hours. After this time, the elimination of water has ended (36 parts of water). After distilling off excess alcohol and amine, the N-(2-phenylethyl)-m-toluidine distils at a boiling point of 167° C/5 mm Hg. 402 parts of N-(2-phenylethyl)-m-toluidine (90% of theory) are obtained.

Workup

  1. temperatureheated
  2. custominitially to 210° C
  3. distillationAfter distilling off excess alcohol and amine
  4. customthe N-(2-phenylethyl)-m-toluidine distils at a boiling point of 167° C/5 mm Hg

Sources & evidence

ORD record
ord-347fd97e2dc54ee39ef09a11ce87627d
Source dataset
uspto-grants-1978_01
Patent number
US04067903

Reaction notes

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