Acetic Anhydride → HCID 54330244, compound

HRID 1276544Notes

Reaction equation

HRID 1276544 reaction equation
[CH:1](=[O:10])[C:2]1[CH:9]=[CH:8][CH:7]=[C:4]([CH:5]=[O:6])[CH:3]=1.C([O:14][C:15](=[O:17])[CH3:16])(=O)C>C(Cl)(Cl)(Cl)Cl>[C:5]([O:6][CH:5]([O:14][C:15](=[O:17])[CH3:16])[C:4]1[CH:7]=[CH:8][CH:9]=[C:2]([CH:1]([O:17][C:15](=[O:14])[CH3:16])[O:10][C:1](=[O:10])[CH3:2])[CH:3]=1)(=[O:6])[CH3:4]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 34777Isophthalaldehyde

Product 1

HCID 54330244HCID 54330244, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
30 °C

Procedure

Isophtalaldehyde (10.0 g, 0.075 mol) and acetic acid anhydride (16.7 g, 0.164 mol) were mixed under N2 -atmosphere in carbontetrachloride (25 ml). Nafion NR 50 was added and the reaction mixture stirred at 30° C. for several days. During this period additional amounts of catalyst (100 mg) and solvent (5 ml) were added. The catalyst was filtered off and also the reaction mixture was filtered, washing with ether. The crude solid was recrystallized from cyclohexane (540 ml), giving white crystals, m.p. 110-130° C. The yield was 10.3 g, 41% of the theoretical. 1H- and 13C NMR (CDCl3), d (ppm) rel. to TMS: 7.72 (s, 1H, CH(OAc)2), 7.70-7.42 (m, 1+2+1H, Ar-H) and 2.13 (s, 6H, CH3); 168.591 (C=O), 135.908, 128.885, 128.047 and 124.879 (Ar), 89.072 (CH(OAc)2) and 20.717 (CH3).

Workup

  1. filtrationThe catalyst was filtered off
  2. filtrationalso the reaction mixture was filtered
  3. washwashing with ether
  4. customThe crude solid was recrystallized from cyclohexane (540 ml)
  5. customgiving white crystals, m.p. 110-130° C

Sources & evidence

ORD record
ord-b54d5ddac2ec45e3a1c391831a4ee44f
Source dataset
uspto-grants-2000_12
Patent number
US06166074

Reaction notes

Loading…