Reaction #2460294

Reaction equation

thiosalicylic acid

3-methoxyiodobenzene

potassium carbonate

N,N-dimethylformamide

→

2-[(3-methoxyphenyl)thio]benzoic acid

Yield 40.0%

Solvents

ether

Conditions

Workup

1. 1
   OtherFirst, 2-[(3-methoxyphenyl)thio]benzoic acid was prepared
2. 2
   Temperaturewas heated
3. 3
   Temperatureat reflux for 2 h
4. 4
   Temperaturecooled
5. 5
   Washwashed twice with 10% aqueous HCl
6. 6
   Dryingdried (Na2SO4)
7. 7
   OtherThe solvent is removed at reduced pressure
8. 8
   OtherThe product was purified by recrystallization from heptane

Procedure

First, 2-[(3-methoxyphenyl)thio]benzoic acid was prepared. A mixture of thiosalicylic acid (1.5 g, 9.7 mmol), 3-methoxyiodobenzene (4.6 g, 19.4 mmol), copper (I) iodide (0.07 g, 0.4 mmol), potassium carbonate (4.0 g, 29.2 mmol), and N,N-dimethylformamide (25 mL) was heated at reflux for 2 h and then cooled to ambient. The reaction mixture was diluted with ether, washed twice with 10% aqueous HCl, and dried (Na2SO4). The solvent is removed at reduced pressure to deposit a brown solid. The product was purified by recrystallization from heptane to provide 1.0 g (40% of theory) of 2-[(3-methoxyphenyl)thio]benzoic acid as a tan solid. 1H NMR (CDCl3): δ 3.80 (s, 3H), 6.90 (d, 1H), 7.00 (d, 1H), 7.25 (m, 5H), 8.11 (d, 1H).

Source