Реакция #417965

Уравнение реакции

Acetic anhydride

5-amino-2-methyl phenol

3-bromophenetole

Cs2CO3

→

product 18a

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

Растворители

acetic acid

water

DMF

Условия реакции

Обработка

1. 1
   Температураthe reaction was refluxed for 5 mins
2. 2
   ФильтрацияIt was filtered off
3. 3
   Промывкаwashed with water (4 mL)
4. 4
   Другоеdried
5. 5
   Другоеto obtain the product along with the trace amount of O-acylated product
6. 6
   Экстракцияextracted with ethyl acetate (3×20 mL)
7. 7
   СушкаThe combined extracts were dried over sodium sulfate
8. 8
   Другоеrecrystallized from toluene

Методика

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.

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