Hydrochloric Acid → HCID 19792498, compound

HRID 1655498Notes

Reaction equation

HRID 1655498 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:17])[CH2:14][CH2:15][CH3:16].Cl>C1(C)C=CC=CC=1.O>[C:2]1([CH2:8][CH2:9][C:10](=[O:12])[CH2:11][C:13](=[O:17])[CH2:14][CH2:15][CH3:16])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7762Ethyl butyrateHCID 17355Benzyl acetoneHCID 5360545Sodium

Product 1

HCID 19792498HCID 19792498, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Sodium (7.3 g) was added in small portions to a solution of 4-phenyl-2-butanone (46.8 g, 0.31 mol) and ethyl butyrate (110 g, 0.95 mol) in toluene (120 ml) at 20°-60° C. under nitrogen, and stirring was continued for 9 h under reflux. After standing overnight, the reaction mixture was taken up in H2O (300 ml), neutralized with hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with H2O, dried over anhydrous MgSO4 and then evaporated. The residual reddish orange oil (84 g) was distilled under reduced pressure to afford the title compound as a pale yellow oil which was an ca 3:7 mixture of Keto/Enol as seen by the methylene singlet at δ3.52 ppm and the methine singlet as δ5.45 ppm in the 1HNMR spectrum; yield: 15.4 g; bp. 166°-168° C./2 mmHg.

Workup

  1. temperatureunder reflux
  2. waitAfter standing overnight
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with H2O
  5. dry with materialdried over anhydrous MgSO4
  6. customevaporated
  7. distillationThe residual reddish orange oil (84 g) was distilled under reduced pressure

Sources & evidence

ORD record
ord-91787090d11544ec836f333b14b54ae8
Source dataset
uspto-grants-1993_10
Patent number
US05250669

Reaction notes

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