Cesium carbonate → Cesium thiobenzoate

HRID 409186Notes

Reaction equation

HRID 409186 reaction equation
[C:1]([OH:9])(=[S:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+:14].[Cs+]>CO>[C:1]([O-:9])(=[S:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cs+:14]

Participants

4

Reactant 2

HCID 10796Cesium carbonateHCID 178526132HCID 178526132, compound

Product 1

HCID 23707493Cesium thiobenzoateYield 83.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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).

Workup

  1. dissolutionwere dissolved
  2. concentrationThe resulting solution was concentrated on the rotovap
  3. additionThe solid residue was diluted with 500 mL of acetone
  4. filtrationthe white solid (CsHCO3) was filtered off
  5. customwas removed
  6. concentrationThe acetone was then concentrated

Sources & evidence

ORD record
ord-fc79c9c8444c4c0b97019550879c06d6
Source dataset
uspto-grants-2014_06
Patent number
US08759378B2

Reaction notes

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