Benzaldehyde → Bis-(hydroxyethyl)amino benzyl malonic acid

HRID 27732

Reaction equation

HRID 27732 reaction equation
[C:1]([OH:7])(=[O:6])[CH2:2][C:3]([OH:5])=[O:4].[NH:8]([CH2:12][CH2:13][OH:14])[CH2:9][CH2:10][OH:11].[CH:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CO>[OH:11][CH2:10][CH2:9][N:8]([C:2]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:1]([OH:7])=[O:6])[C:3]([OH:5])=[O:4])[CH2:12][CH2:13][OH:14]

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 867Malonic AcidHCID 8113Diethanolamine

Product 1

HCID 70589253Bis-(hydroxyethyl)amino benzyl malonic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

Bis-(hydroxyethyl)amino benzyl malonic acid was prepared conventionally in a flask equipped with a stirrer and reflux condenser by first charging 0.1 mol of malonic acid, 0.1 mol of diethanol amine and 100 cc methanol. The contents were warmed to a temperature of about 20° C. and then 0.1 mol benzaldehyde were added to the flask and the reaction commenced. After refluxing the reaction mixture for 1 hour, the methanol was removed from the reaction mixture by coupling the flask to a vacuum source and heating to a temperature of about 50° C. The residue remaining in the flask then was triturated in acetone and the resulting acid isolated by filtration.

Workup

  1. customequipped with a stirrer
  2. temperaturereflux condenser
  3. customthe reaction commenced
  4. temperatureAfter refluxing the reaction mixture for 1 hour
  5. customthe methanol was removed from the reaction mixture
  6. temperatureheating to a temperature of about 50° C
  7. customthen was triturated in acetone
  8. customthe resulting acid isolated by filtration

Sources & evidence

ORD record
ord-f6f1eba0660f45359039c5f80d9361d8
Source dataset
uspto-grants-1980_09
Patent number
US04223139

Linked notes

Loading…