Benzoic Acid → Bismuth tribenzoate

HRID 412992Notes

Reaction equation

HRID 412992 reaction equation
C([O-])(=O)C.[Bi+3:5].C([O-])(=O)C.C([O-])(=O)C.[C:14]([OH:22])(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1(C)C=CC=CC=1>[C:14]([O-:22])(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Bi+3:5].[C:14]([O-:22])(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[C:14]([O-:22])(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 243Benzoic AcidHCID 31132Bismuth acetate

Product 1

HCID 9916093Bismuth tribenzoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

5.79 grams of bismuth acetate (Aldrich) and three equivalents, 5.49 grams, of benzoic acid (Aldrich) were added to a 500 milliliter one neck round bottom flask. Toluene (300 milliliters) was then added as the solvent. A distillation head with 500 milliliters catch flask was attached to the reaction flask. The mixture was stirred vigorously and heated to reflux (about 110° C.). The mixture never completely dissolved (white cloudy mix). After about 5 hours of refluxing (while stirring), the toluene was slowly distilled off. When about 50 milliliters were left in the reaction flask, the heat was turned off and the reaction was allowed to cool to room temperature. A white powder precipitated and was separated by filtration. The resulting white powder was rinsed with about 1 liter of hexane, collected and dried overnight in vacuo at 50° C. The yield was 7.2 grams.

Workup

  1. temperatureheated
  2. dissolutionThe mixture never completely dissolved
  3. addition(white cloudy mix)
  4. temperatureAfter about 5 hours of refluxing
  5. stirring(while stirring)
  6. distillationthe toluene was slowly distilled off
  7. waitWhen about 50 milliliters were left in the reaction flask
  8. temperatureto cool to room temperature
  9. customA white powder precipitated
  10. customwas separated by filtration
  11. washThe resulting white powder was rinsed with about 1 liter of hexane
  12. customcollected
  13. customdried overnight in vacuo at 50° C

Sources & evidence

ORD record
ord-699d6d07a0ec45f4823134837d543589
Source dataset
uspto-grants-2003_05
Patent number
US06565895B2

Reaction notes

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