Cesium carbonate → Cesium thiobenzoate

HRID 508134Notes

Reaction equation

HRID 508134 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-85526bdd15824d929ca1206a744dae88
Source dataset
uspto-grants-2015_08
Patent number
US09095565B2

Reaction notes

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