Acetic Anhydride → 4-(N-4-acetoxybutyl-N-butylamino)benzaldehyde

HRID 6201Notes

Reaction equation

HRID 6201 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]([C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][CH:12]=1)[CH2:7][CH2:8][CH2:9][CH3:10].[C:19](OC(=O)C)(=[O:21])[CH3:20].C(N(CC)CC)C>ClCCl>[C:19]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]([C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][CH:12]=1)[CH2:7][CH2:8][CH2:9][CH3:10])(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 197950944-(N-4-hydroxybutyl-N-butylamino)benzaldehyde

Product 1

HCID 110117524-(N-4-acetoxybutyl-N-butylamino)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 249.4 g (1 mole) of 4-(N-4-hydroxybutyl-N-butylamino)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 is washed with cold 2N HCl and then with filtered through cotton, and evaporated to dryness.

Workup

  1. washThe product solution is washed with cold 2N HCl
  2. filtrationwith filtered through cotton
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-3b600f4c7ca4476a9e47d62d4b288b7e
Source dataset
uspto-grants-1993_09
Patent number
US05247042

Reaction notes

Loading…