Reaktion #2460291

Reaktionsgleichung

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

acetic anhydride

sulfuric acid

→

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

Lösungsmittel

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was cooled to ambient and
2. 2
   ExtraktionThe aqueous phase was extracted twice with dichloromethane
3. 3
   Waschenthe combined organic extracts were washed with water
4. 4
   TrocknenThe solution was dried (Na2SO4)
5. 5
   Einengenconcentrated deposit a brown solid
6. 6
   SonstigeThe product was purified by column chromatography
7. 7
   Sonstigeto provide 3.5 g (76% of theory) of a white solid

Vorschrift

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).

Quelle