O-Xylene → HCID 416666, compound

HRID 1598319Notes

Reaction equation

HRID 1598319 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][OH:5].[Cl:6][C:7]1[CH:14]=[CH:13][C:10]([CH2:11]Cl)=[CH:9][CH:8]=1.C1(C)C(C)=CC=CC=1>Cl>[Cl:6][C:7]1[CH:14]=[CH:13][C:10]([CH2:11][N:2]([CH3:1])[CH2:3][CH2:4][OH:5])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 7237O-XyleneHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 80162-(Methylamino)ethanol

Product 1

HCID 416666HCID 416666, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of N-methylethanolamine (21.2 g), 4-chlorobenzyl chloride (35.0 g) and xylene (100 ml) was stirred and boiled under reflux for 7 hours. The mixture was allowed to cool to ambient temperature and the solid mass was dissolved in 2M hydrochloric acid. The aqueous phase was separated off, washed with ether, basified with 2M sodium hydroxide solution and extracted with dichloromethane to give an oil which was distilled at 120°-125° C. at 0.3 mbar to give N-(4-chlorobenzyl)-N-methylethanolamine.

Workup

  1. temperatureunder reflux for 7 hours
  2. customThe aqueous phase was separated off
  3. washwashed with ether
  4. extractionextracted with dichloromethane
  5. customto give an oil which
  6. distillationwas distilled at 120°-125° C. at 0.3 mbar

Sources & evidence

ORD record
ord-410b6e46d94a40ec93c1388fc3b89b3f
Source dataset
uspto-grants-1998_04
Patent number
US05736568

Reaction notes

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