Réaction #2460293

Équation de réaction

2-(4-butoxyphenoxy)benzoic acid

sulfuric acid

→

2-butoxyxanthen-9-one

Solvants

acetic anhydride

Conditions de réaction

Traitement

1. 1
   TempératureThe mixture was cooled to ambient, and
2. 2
   AutreThe precipitated crude product
3. 3
   Autrewas collected
4. 4
   Lavagewashed with water, and air
5. 5
   Autredried
6. 6
   AutreThe product was purified by column chromatography
7. 7
   Autrefollowed by recrystallization from 50% aqueous ethanol
8. 8
   AutreA white powder was obtained

Mode opératoire

Finally, 2-butoxyxanthen-9-one (S-14) was synthesized. A stirred suspension under argon of 2-(4-butoxyphenoxy)benzoic acid (8.2 g, 29 mmol) in acetic anhydride (50 mL) was treated with 2.8 g (29 mmol) of concentrated sulfuric acid, and then held at 80° C. for 3 h. The mixture was cooled to ambient, and then poured onto 500 g of ice. The precipitated crude product was collected, washed with water, and air dried. The product was purified by column chromatography followed by recrystallization from 50% aqueous ethanol. A white powder was obtained. 1H NMR (CDCl3): δ 1.00 (t, 3H), 1.5 (m, 2H), 1.85 (m, 2H), 4.08 (t, 2H), 7.3-7.5 (m, 4H), 7.7 (m, 2H), 8.36 (d, 1H).

Source