Reacción #2460291

Ecuación de reacción

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

acetic anhydride

sulfuric acid

→

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

Disolventes

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction mixture was cooled to ambient and
2. 2
   ExtracciónThe aqueous phase was extracted twice with dichloromethane
3. 3
   Lavadothe combined organic extracts were washed with water
4. 4
   SecadoThe solution was dried (Na2SO4)
5. 5
   Concentraciónconcentrated deposit a brown solid
6. 6
   OtroThe product was purified by column chromatography
7. 7
   Otroto provide 3.5 g (76% of theory) of a white solid

Procedimiento

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).

Fuente