Reaktion #2460298

Reaktionsgleichung

thiosalicylic acid

3-iodoanisole

potassium carbonate

→

2-(3-methoxyphenylthio)benzoic acid

Lösungsmittel

N-methylpyrrolidinone

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeby sparging with nitrogen for 10 min
2. 2
   Temperaturcooled
3. 3
   workup.ADDITIONThe reaction mixture was poured onto a mixture of 500 g of ice plus 40 mL of concentrated HCl
4. 4
   SonstigeThe resulting precipitate was collected
5. 5
   Waschenwashed with water
6. 6
   Sonstigedried
7. 7
   workup.DISSOLUTIONThe precipitate was dissolved in acetone
8. 8
   Filtrationfiltered through Celite
9. 9
   Einengenconcentrated
10. 10
    SonstigeThe product was purified by recrystallization from aqueous ethanol
11. 11
    SonstigeA tan powder was obtained

Vorschrift

First, 2-(3-methoxyphenylthio)benzoic acid was prepared. A stirred mixture of thiosalicylic acid (3.57 g, 23 mmol), 3-iodoanisole (5.42 g, 23 mmol), potassium carbonate (7.04 g, 51 mmol), copper powder (0.29 g, 5 mmol), and N-methylpyrrolidinone (75 mL) was deaerated by sparging with nitrogen for 10 min, heated at 165° C. for 2 h, and then cooled to ambient. The reaction mixture was poured onto a mixture of 500 g of ice plus 40 mL of concentrated HCl. The resulting precipitate was collected, washed with water, and dried. The precipitate was dissolved in acetone and filtered through Celite, then concentrated to deposit a crude product. The product was purified by recrystallization from aqueous ethanol. A tan powder was obtained, mass: 4.60 g (76% of theory).

Quelle