Acetic Anhydride → Benzaldehyde, 4-[[2-(acetyloxy)ethyl]ethylamino]-

HRID 359634Notes

Reaction equation

HRID 359634 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([C:7]1[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[CH:9][CH:8]=1)[CH2:5][CH3:6].[C:15](OC(=O)C)(=[O:17])[CH3:16].C(N(CC)CC)C>ClCCl>[C:15]([O:1][CH2:2][CH2:3][N:4]([C:7]1[CH:8]=[CH:9][C:10]([CH:11]=[O:12])=[CH:13][CH:14]=1)[CH2:5][CH3:6])(=[O:17])[CH3:16]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 6398574-(Ethyl(2-hydroxyethyl)amino)benzaldehyde

Product 1

HCID 11458991Benzaldehyde, 4-[[2-(acetyloxy)ethyl]ethylamino]-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 193.2 g (1 mole) of 4-(N-2-hydroxyethyl-N-ethylamino)benzaldehyde in dichloromethane are added 153.1 g (1.5 moles) of acetic anhydride, 151.8 g (1.5 moles) of triethylamine, and 8.5 g (7 mole %) of 4-N,N-dimethylaminopyridine. The reaction mixture is stirred at room temperature for 16 hours. The product solution then is washed with cold 2N HCl followed by saturated sodium bicarbonate, and the organic layer is filtered through cotton, and evaporated to dryness.

Workup

  1. washThe product solution then is washed with cold 2N HCl
  2. filtrationthe organic layer is filtered through cotton
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-680d79a56aa844df9432510ad28fa63b
Source dataset
uspto-grants-1991_03
Patent number
US05002361

Reaction notes

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