반응 #417965

반응 방정식

Acetic anhydride

5-amino-2-methyl phenol

3-bromophenetole

Cs2CO3

→

product 18a

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

용매

acetic acid

water

DMF

반응 조건

후처리

1. 1
   온도the reaction was refluxed for 5 mins
2. 2
   여과It was filtered off
3. 3
   세척washed with water (4 mL)
4. 4
   기타dried
5. 5
   기타to obtain the product along with the trace amount of O-acylated product
6. 6
   추출extracted with ethyl acetate (3×20 mL)
7. 7
   건조The combined extracts were dried over sodium sulfate
8. 8
   기타recrystallized from toluene

실험 절차

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.

출처