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

HRID 1084674Notes

Reaction equation

HRID 1084674 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

Conditions

Temperature
95 °C

Procedure

A 2 liter three-necked flask fitted with a mechanical stirrer, therometer 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 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. customA 2 liter three-necked flask fitted with a mechanical stirrer
  2. temperatureThe product mixture is cooled
  3. filtrationThe resultant solid precipitate is filtered
  4. washwashed with water, and vacuum
  5. customdried
  6. customThe crude product is recrystallized from toluene, m.p. 72° C.

Sources & evidence

ORD record
ord-97fdda6beffa48888649651cdae5ed04
Source dataset
uspto-grants-1991_04
Patent number
US05006285

Reaction notes

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