Acetone → 2,4-Pentanedione, 1-phenyl-

HRID 1779273Notes

Reaction equation

HRID 1779273 reaction equation
[Na].[C:2]1([CH2:8][C:9]([O:11]CC)=O)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:14][C:15]([CH3:17])=[O:16].Cl>O>[C:2]1([CH2:8][C:9](=[O:11])[CH2:14][C:15](=[O:16])[CH3:17])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 7590Ethyl phenylacetateHCID 5360545Sodium

Product 1

HCID 187232,4-Pentanedione, 1-phenyl-Yield 24.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium (28 g) was added in small portions to a solution of ethyl phenylacetate (600 g, 3.66 moles) and acetone (70.7 g, 1.22 moles) under nitrogen, was dissolved at 30°-40° C. with stirring for 1 hour and then the mixture was reacted at 70°-80° C. for 4.5 hours. The reaction mixture was taken up in H2O (1.2 l), neutralized with dilute hydrochloric acid and extracted with chloroform. The organic layer was washed with H2O, dried over anhydrous MgSO4 and then evaporated. The residue was distilled under reduced pressure to give 53.2 g of the desired product as a colorless oil having a boiling point of 142°-146° C./15 mmHg. [Lit.: bp. 133°-136° C./10 mmHg; K. G. Hampton, T. M. Harris, C. R. Hauser, Org. Synth., 51., 128 (1971).]

Workup

  1. dissolutionwas dissolved at 30°-40° C.
  2. customthe mixture was reacted at 70°-80° C. for 4.5 hours
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with H2O
  5. dry with materialdried over anhydrous MgSO4
  6. customevaporated
  7. distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-19f4db7998fd4ed4ab1e4ace9d0fb611
Source dataset
uspto-grants-1997_05
Patent number
US05627006

Reaction notes

Loading…