Reaction #2460296

Reaction equation

thiosalicylic acid

4-iodoanisole

potassium carbonate

→

2-(4-methoxyphenylthio)benzoic acid

Solvents

N-methylpyrrolidinone

Conditions

Workup

1. 1
   Otherby sparging with nitrogen for 10 min
2. 2
   Temperaturecooled
3. 3
   workup.ADDITIONThe reaction mixture was poured onto a mixture of 500 g of ice plus 40 mL or concentrated HCl
4. 4
   OtherThe resulting precipitate was collected
5. 5
   Washwashed with water
6. 6
   Otherdried
7. 7
   OtherThe product was purified by recrystallization from a mixture of water, ethanol, and tetrahydrofuran
8. 8
   OtherA white powder was obtained

Procedure

First, 2-(4-methoxyphenylthio)benzoic acid was prepared. A stirred mixture of thiosalicylic acid (10.0 g, 65 mmol), 4-iodoanisole (15.18 g, 65 mmol), potassium carbonate (19.72 g, 143 mmol), copper powder (0.82 g, 13 mmol), and N-methylpyrrolidinone (100 mL) was deaerated by sparging with nitrogen for 10 min, heated at 165° C. for 18 h, and then cooled to ambient. The reaction mixture was poured onto a mixture of 500 g of ice plus 40 mL or concentrated HCl. The resulting precipitate was collected, washed with water, and dried. The product was purified by recrystallization from a mixture of water, ethanol, and tetrahydrofuran. A white powder was obtained, mass: 12.06 g (71% of theory).

Source