Reaction #2460300

Reaction equation

4-iodobenzoic acid

thiosalicylic acid

→

2,4′-thiobis(benzoic acid)

Solvents

sodium hydroxide

Conditions

Workup

1. 1
   Temperaturewas heated
2. 2
   Temperatureat reflux for 5 h
3. 3
   Temperaturecooled
4. 4
   FiltrationThe reaction mixture was filtered
5. 5
   OtherThe precipitate was collected
6. 6
   Washwashed with water
7. 7
   workup.DISSOLUTIONdissolved
8. 8
   Filtrationfiltered
9. 9
   ConcentrationThe filtrate was concentrated

Procedure

First, 2,4′-thiobis(benzoic acid) was prepared. A mixture of 4-iodobenzoic acid (55.7 g, 225 mmol), thiosalicylic acid (34.6 g, 225 mmol), copper powder (15 g, 236 mmol), zinc powder (3 g, 46 mmol), and 2.5 M aqueous sodium hydroxide (400 mL) was heated at reflux for 5 h and then cooled to ambient. The reaction mixture was filtered, and the filtrate was acidified with concentrated HCl. The precipitate was collected and washed with water, then dissolved and filtered. The filtrate was concentrated to deposit 2,4′-thiobis(benzoic acid), mass 50 g (81% of theory).

Source