反応 #2460291

反応方程式

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

acetic anhydride

sulfuric acid

→

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

溶媒

反応条件

後処理

1. 1
   温度The reaction mixture was cooled to ambient and
2. 2
   抽出The aqueous phase was extracted twice with dichloromethane
3. 3
   洗浄the combined organic extracts were washed with water
4. 4
   乾燥The solution was dried (Na2SO4)
5. 5
   濃縮concentrated deposit a brown solid
6. 6
   その他The product was purified by column chromatography
7. 7
   その他to provide 3.5 g (76% of theory) of a white solid

実験手順

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).

出典