Acetic Acid → 4-(N,N-Bis(2-hydroxyethyl)amino)benzaldehyde

HRID 359573Notes

Reaction equation

HRID 359573 reaction equation
C([O:4][CH2:5][CH2:6][N:7]([CH2:16][CH2:17][O:18]C(=O)C)[C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=1)(=O)C.C[O-].[Na+].C(O)(=O)C>CN(C)C=O.CO>[OH:4][CH2:5][CH2:6][N:7]([CH2:16][CH2:17][OH:18])[C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 3287294-[Bis[2-(acetyloxy)ethyl]amino]benzaldehydeHCID 10942334Sodium Methoxide

Product 1

HCID 128249654-(N,N-Bis(2-hydroxyethyl)amino)benzaldehydeYield 74.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 293 g of 4-di-(2-acetoxyethyl) aminobenzaldehyde (see under Example 2b) in 500 ml of dimethyl formamide was added a solution of 54 g of sodium methanolate in 500 ml of methanol. After stirring for 30 minutes at room temperature the reaction mixture was neutralized with acetic acid and concentrated to a small volume. The residue was taken up in 500 ml of water and 500 ml of ethyl acetate. The water layer was separated and extracted six times, each time with a portion of 500 ml of ethyl acetate. The combined organic layers were dried on magnesium sulphate and evaporated. The residue was crystallized from 500 ml of ethyl acetate to yield 156 g of 4-di(2-hydroxyethyl)aminobenzaldehyde with a melting point of 63°-64° C.

Workup

  1. concentrationconcentrated to a small volume
  2. customThe water layer was separated
  3. extractionextracted six times
  4. customThe combined organic layers were dried on magnesium sulphate
  5. customevaporated
  6. customThe residue was crystallized from 500 ml of ethyl acetate

Sources & evidence

ORD record
ord-e3babbee69f248b695f966ff29e16041
Source dataset
uspto-grants-1991_03
Patent number
US05001209

Reaction notes

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