Réaction #417965

Équation de réaction

Acetic anhydride

5-amino-2-methyl phenol

3-bromophenetole

Cs2CO3

→

product 18a

N-[4-methyl-3-(2-phenoxy-ethoxy)-phenyl]-acetamide

Solvants

acetic acid

water

DMF

Conditions de réaction

Traitement

1. 1
   Températurethe reaction was refluxed for 5 mins
2. 2
   FiltrationIt was filtered off
3. 3
   Lavagewashed with water (4 mL)
4. 4
   Autredried
5. 5
   Autreto obtain the product along with the trace amount of O-acylated product
6. 6
   Extractionextracted with ethyl acetate (3×20 mL)
7. 7
   SéchageThe combined extracts were dried over sodium sulfate
8. 8
   Autrerecrystallized from toluene

Mode opératoire

Acetic anhydride (1.25 mL, 12.2 mmol) was added to a solution of 5-amino-2-methyl phenol (1.0 g, 8.1 mmol) in acetic acid (6 mL), and the reaction was refluxed for 5 mins. Then the reaction mixture was cooled to room temperature and the product was solidified. It was filtered off and washed with water (4 mL) and dried to obtain the product along with the trace amount of O-acylated product. The mixture, to which was added 3-bromophenetole (1.33 g, 6.6 mmol) and Cs2CO3 (2.927 g, 9.0 mmol) in DMF (10 mL), was stirred overnight at 50° C. The reaction mixture was then diluted with water (10 mL) and extracted with ethyl acetate (3×20 mL). The combined extracts were dried over sodium sulfate and recrystallized from toluene to obtain the pure product 18a in 65% (yield over two steps) as an off-white solid.

Source