Water → Ethanone, 2-hydroxy-2-phenyl-1-(3-pyridinyl)-

HRID 237007Notes

Reaction equation

HRID 237007 reaction equation
Br.Br[CH:3]([C:10]([C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C([O-])(=[O:20])C.[K+].O>C(OC(=O)C)(=O)C>[OH:20][CH:3]([C:10]([C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 517044Potassium AcetateHCID 134660052-Bromo-2-phenyl-1-(3-pyridyl)ethanone hydrobromide

Product 1

HCID 20460416Ethanone, 2-hydroxy-2-phenyl-1-(3-pyridinyl)-Yield 68.3%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

Alternatively, a mixture of 20.0 g (56.0 mmoles) of 3-pyridyl α-bromobenzyl ketone hydrobromide and 24.0 g (0.24 mole) of potassium acetate in 100 ml of acetic anhydride was stirred overnight at room temperature. The reaction mixture was poured into water and the product extracted into ether. The combined ether layers were washed with water and then 10% aqueous sodium bicarbonate solution. The ether layer was dried over potassium carbonate and evaporated. A solution of the residue in 140 ml of 1 N aqueous hydrochloric acid was heated at reflux for 30 minutes and after cooling made basic with solid sodium carbonate. The product was extracted into ether and the combined ether extracts evaporated, after drying over anhydrous potassium carbonate, to give 8.15 g of 3-pyridyl α-hydroxybenzyl ketone.

Workup

  1. extractionthe product extracted into ether
  2. washThe combined ether layers were washed with water
  3. dry with materialThe ether layer was dried over potassium carbonate
  4. customevaporated
  5. temperatureA solution of the residue in 140 ml of 1 N aqueous hydrochloric acid was heated
  6. temperatureat reflux for 30 minutes
  7. temperatureafter cooling
  8. extractionThe product was extracted into ether
  9. customthe combined ether extracts evaporated
  10. dry with materialafter drying over anhydrous potassium carbonate

Sources & evidence

ORD record
ord-1ccac70cca1c495e93f97daeeddfa1a3
Source dataset
uspto-grants-1979_06
Patent number
US04159338

Reaction notes

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