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

HRID 1607470Notes

Reaction equation

HRID 1607470 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, 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 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 produce it 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 produce it
  6. customrecrystallized from toluene, m.p. 72° C.

Sources & evidence

ORD record
ord-17786e753c484827af1c010773205879
Source dataset
uspto-grants-1989_09
Patent number
US04865430

Reaction notes

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