Reaction #595316

Reaction equation

thiobenzoic acid

Cs2CO3

→

cesium thiobenzoate

Yield 83.4%

Solvents

methanol

Conditions

Workup

1. 1
   workup.DISSOLUTIONwere dissolved
2. 2
   ConcentrationThe resulting solution was concentrated on the rotovap
3. 3
   workup.ADDITIONThe solid residue was diluted with 500 mL of acetone
4. 4
   Filtrationthe white solid (CsHCO3) was filtered off
5. 5
   Otherwas removed
6. 6
   ConcentrationThe acetone was then concentrated

Procedure

To a solution of thiobenzoic acid (50.0 g, 361.8 mmol) in methanol (362 mL) was added Cs2CO3 (130 g, 398 mmol) in portions over 5 min. The resulting mixture was stirred 10 min until all solids were dissolved. The resulting solution was concentrated on the rotovap. The solid residue was diluted with 500 mL of acetone and the white solid (CsHCO3) was filtered off. This process was repeated two times to ensure all CsHCO3 was removed. The acetone was then concentrated to afford cesium thiobenzoate (Strijtveen, B.; Kellogg, R. M. J. Org. Chem. 1986, 51, 3664) as a yellow solid (81.5 g, 83%); 1H NMR (300 MHz, CD3OD) δ 7.25-7.38 (m, 3H), 8.09 (dd, J=1.4, 8.2 Hz, 2H).

Source