2-(Methylamino)ethanol → 4-[(2-Hydroxyethyl)(methyl)amino]benzaldehyde

HRID 654634Notes

Reaction equation

HRID 654634 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][OH:5].F[C:7]1[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[CH:9][CH:8]=1.C(=O)([O-])[O-].[K+].[K+]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].CS(C)=O>[OH:5][CH2:4][CH2:3][N:2]([C:7]1[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[CH:9][CH:8]=1)[CH3:1]

Participants

6

Reactant 3

HCID 80162-(Methylamino)ethanolHCID 11430Potassium CarbonateHCID 680234-Fluorobenzaldehyde

Product 1

HCID 36143164-[(2-Hydroxyethyl)(methyl)amino]benzaldehyde

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

A 2 liter three (3) necked flask fitted with a mechanical stirrer, thermometer and condenser is charged with 134 g of 2-(methylamino)ethanol, 74.4 g of 4-fluorobenzaldehyde, 1 ml of Aliquat 336, 750 ml of dimethylsulfoxide and 82.8 g of anhydrous potassium carbonate. The mixture is heated at 95° C. for three (3) days. The product mixture is cooled and poured into 3 liters of ice water. The resultant solid precipitate is filtered, washed with water, and vacuum dried. The crude product is recrystallized from toluene, m.p. 72° C.

Workup

  1. temperatureThe product mixture is cooled
  2. filtrationThe resultant solid precipitate is filtered
  3. washwashed with water, and vacuum
  4. customdried
  5. customThe crude product is recrystallized from toluene, m.p. 72° C.

Sources & evidence

ORD record
ord-c0c1940ec9f0403d80f56a54ec6054f6
Source dataset
uspto-grants-1992_07
Patent number
US05133037

Reaction notes

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