Hydrochloric Acid → 6-phenylhexane-2,4-dione

HRID 1655492Notes

Reaction equation

HRID 1655492 reaction equation
[Na].[C:2]1([CH2:8][CH2:9][C:10](=[O:12])[CH3:11])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:13](OCC)(=[O:15])[CH3:14].Cl>O>[C:2]1([CH2:8][CH2:9][C:10](=[O:12])[CH2:11][C:13](=[O:15])[CH3:14])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 17355Benzyl acetoneHCID 5360545Sodium

Product 1

HCID 4209466-phenylhexane-2,4-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium (23 g) was added in small portions to a solution of 4-phenyl-2-butanone (148 g, 1 mol) and ethyl acetate (264 g) at 20°-60° C. with stirring under nitrogen and then the reaction mixture was refluxed for 2 h with stirring. After cooling, the mixture was taken up in H2O (1l), neutralized with hydrochloric acid, the organic layer was separated, washed with H2O, dried over anhydrous Na2SO4 and then evaporated. The resultant residue (171 g) was distilled under reduced pressure to give the title compound as a colorless oil; yield: 73.4 g; bp 128°-133° C./3-4 mmHg (Lit. bp 133°-136° C./5 mmHg; C. R. Hauser, T. M. Harris, J. Am. Chem. Soc., 80, 6360 (1958)).

Workup

  1. temperaturethe reaction mixture was refluxed for 2 h
  2. stirringwith stirring
  3. temperatureAfter cooling
  4. customthe organic layer was separated
  5. washwashed with H2O
  6. dry with materialdried over anhydrous Na2SO4
  7. customevaporated
  8. distillationThe resultant residue (171 g) was distilled under reduced pressure

Sources & evidence

ORD record
ord-023682c4c26e4a42aeb729996f4c53ce
Source dataset
uspto-grants-1993_10
Patent number
US05250669

Reaction notes

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