반응 #2460291

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2,4-di-(tert-amyl)phenoxybenzoic acid

acetic anhydride

sulfuric acid

→

2,4-di-(tert-amyl)xanthen-9-one

용매

반응 조건

후처리

1. 1
   온도The reaction mixture was cooled to ambient and
2. 2
   추출The aqueous phase was extracted twice with dichloromethane
3. 3
   세척the combined organic extracts were washed with water
4. 4
   건조The solution was dried (Na2SO4)
5. 5
   농축concentrated deposit a brown solid
6. 6
   기타The product was purified by column chromatography
7. 7
   기타to provide 3.5 g (76% of theory) of a white solid

실험 절차

Finally, 2,4-di-(tert-amyl)xanthen-9-one (S-13) was prepared. To a suspension of 2,4-di-(tert-amyl)phenoxybenzoic acid (4.8 g, 13.6 mmol) in acetic anhydride (27.7 g, 272 mmol) was added dropwise sulfuric acid (1.33 g, 13.6 mmol), and then the mixture was held at 80° C. for 3 h. The reaction mixture was cooled to ambient and poured into 100 mL of ice water. The aqueous phase was extracted twice with dichloromethane, and the combined organic extracts were washed with water and then with brine. The solution was dried (Na2SO4) and concentrated deposit a brown solid. The product was purified by column chromatography to provide 3.5 g (76% of theory) of a white solid. 1H NMR (CDCl3): δ 0.75 (t, 6H), 1.3 (s, 6H), 1.4 (s, 6H), 1.65 (q, 2H), 1.80 (q, 2H), 3.85 (s, 3H), 6.80 (d, 2H), 7.15 (m, 2H), 7.35 (br s, 1H), 7.45 (t, 1H), 8.2 (d, 1H).

출처