Réaction #46907

Équation de réaction

4-hydroxybenzamide

acetylsalicylic acid

hydroxybenzotriazole

DCC

→

4-carbamoylphenyl 2-acetoxybenzoate

Rendement 47.0%

Solvants

chloroform

dimethylformamide

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGstirred for 1 h at 0° C. and 3 h at room temperature
2. 2
   FiltrationAfter filtration
3. 3
   Autrethe filtrate was evaporated under reduced pressure
4. 4
   Autreto remove the solvent
5. 5
   AutreThe oily residue thus obtained
6. 6
   Lavagethe organic layer was washed with brine
7. 7
   Séchagedried on anhydrous MgSO4
8. 8
   Filtrationfiltered
9. 9
   Autrethe solvent evaporated
10. 10
    Lavageeluted with CH2Cl2/MeOH (9/1), from which 4-carbamoylphenyl 2-acetoxybenzoate (5)
11. 11
    Autrewas obtained (410 mg, 47% yield)

Mode opératoire

To the solution of 1 (acetylsalicylic acid, 500 mg, 2.77 mmol) in 15 mL of dimethylformamide, hydroxybenzotriazole (412 mg, 3.05 mmol) and DCC (628 mg, 3.05 mmol) were added with stirring at 0° C. for 1 h. To the reaction mixture 4-hydroxybenzamide (4, 418 mg, 3.05 mmol) was added and stirred for 1 h at 0° C. and 3 h at room temperature. After filtration, the filtrate was evaporated under reduced pressure to remove the solvent. The oily residue thus obtained was dissolved in chloroform; the organic layer was washed with brine, dried on anhydrous MgSO4, filtered and the solvent evaporated. The crude product 5 was loaded on a silica gel open column and eluted with CH2Cl2/MeOH (9/1), from which 4-carbamoylphenyl 2-acetoxybenzoate (5) was obtained (410 mg, 47% yield).

Source