2,6-Dimethylaniline → N-(2',6'-dimethylphenyl)-1-methoxymethylethylamine

HRID 1606267Notes

Reaction equation

HRID 1606267 reaction equation
[NH2:1][C:2]1[C:3]([CH3:9])=[CH:4][CH:5]=[CH:6][C:7]=1[CH3:8].[CH3:10][O:11][CH2:12][CH:13](OS(C1C=CC(C)=CC=1)(=O)=O)[CH3:14]>C1(C)C=CC=CC=1.CCOCC>[CH3:10][O:11][CH2:12][CH:13]([NH:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:9])[CH3:14]

Participants

5

Reactant 2

HCID 68962,6-DimethylanilineHCID 1270077423946-74-9

Product 1

HCID 10899497N-(2',6'-dimethylphenyl)-1-methoxymethylethylamine

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 484 g (4 mole) of 2,6-xylidine and 490 g (2 mole) of p-toluenesulphonic acid-(1-methoxyprop-2-yl)-ester in 1000 ml of toluene is refluxed for 25 hours. The reaction mixture is cooled, then made alkaline and diluted with ether. The organic phase is repeatedly washed with water and dried with magnesium sulphate. Evaporation of the solvent and subsequent distillation of the residue yields the desired N-(1-methoxyprop-2-yl)-2,6-xylidine with a boiling point of 70°-72°C/0.4 Torr.

Workup

  1. temperatureThe reaction mixture is cooled
  2. washThe organic phase is repeatedly washed with water
  3. dry with materialdried with magnesium sulphate
  4. customEvaporation of the solvent and subsequent distillation of the residue

Sources & evidence

ORD record
ord-5d435b69e1b04433ae4ed8e4a39b7333
Source dataset
uspto-grants-1976_04
Patent number
US03952056

Reaction notes

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