Réaction #58820

Équation de réaction

3-aminophenol

butyric acid

DCC

→

3-butyramidophenol

Solvants

DCM

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGthe contents stirred overnight at room temperature
2. 2
   FiltrationThe reaction mixture is then filtered
3. 3
   Lavagewashed with DCM
4. 4
   ConcentrationThe filtrate is concentrated
5. 5
   workup.DISSOLUTIONredissolved in methanol
6. 6
   workup.ADDITIONadded with 10% aqueous sodium bicarbonate solution
7. 7
   workup.STIRRINGstirred vigorously until diacylated byproduct

Mode opératoire

3-aminophenol (550 mg; 5 mmol) is added to a solution of butyric acid (1.4 mL; 15 mmol) in DCM (20 mL) at room temperature and stirred vigorously. To this solution DCC (2.48 g; 12 mmol) is added followed by DMAP (24 mg) and the contents stirred overnight at room temperature. The reaction mixture is then filtered and washed with DCM. The filtrate is concentrated and redissolved in methanol, added with 10% aqueous sodium bicarbonate solution and stirred vigorously until diacylated byproduct disappeared (as detected by LC-MS) to yield 3-butyramidophenol as the only product. The product was used for further transformation without further purification.

Source