2,6-Dimethylaniline → 1-(2,6-Dimethylanilino)propan-2-ol

HRID 1648718Notes

Reaction equation

HRID 1648718 reaction equation
[NH2:1][C:2]1[C:3]([CH3:9])=[CH:4][CH:5]=[CH:6][C:7]=1[CH3:8].Br[CH2:11][CH:12]([OH:14])[CH3:13].[OH-].[Na+]>C1(C)C=CC=CC=1>[OH:14][CH:12]([CH3:13])[CH2:11][NH:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:9]

Participants

5

Reactant 3

HCID 68962,6-DimethylanilineHCID 14798Sodium HydroxideHCID 297401-Bromo-2-propanol

Product 1

HCID 136747711-(2,6-Dimethylanilino)propan-2-ol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution consisting of 121 g (1.0 mole), of 2,6-xylidine, 70 g (0.5 mole) 1-bromo-2-propanol and 100 ml of absolute toluene is heated under reflux for 24 hours. After cooling 300 ml 2 N sodium hydroxide are added. The organic layer is separated, washed with water until neutral, dried over sodium sulfate and evaporated in vacuo. The crude product is fractionally distilled to yield 59.6 g of N-(2'-hydroxypropyl)-2,6-xylidine, b.p. 81°-83°/0.1 Torr.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 24 hours
  3. additionare added
  4. customThe organic layer is separated
  5. washwashed with water until neutral,
  6. dry with materialdried over sodium sulfate
  7. customevaporated in vacuo
  8. distillationThe crude product is fractionally distilled

Sources & evidence

ORD record
ord-1b21cd3288d34704899597b1c5dc2414
Source dataset
uspto-grants-1983_11
Patent number
US04412855

Reaction notes

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