Hydrochloric Acid → 2,4-Pentanedione, 3-benzyl-

HRID 1975711Notes

Reaction equation

HRID 1975711 reaction equation
CC(C)([O-])C.[K+].[CH3:7][C:8](=[O:13])[CH2:9][C:10](=[O:12])[CH3:11].[CH2:14](Cl)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.Cl>CS(C)=O>[CH2:14]([CH:9]([C:8](=[O:13])[CH3:7])[C:10](=[O:12])[CH3:11])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7503Benzyl ChlorideHCID 31261AcetylacetoneHCID 23665647Potassium tert-butoxide

Product 1

HCID 977572,4-Pentanedione, 3-benzyl-

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution containing 5.5g of potassium tert-butoxide in 50ml of DMSO was added 6.0 g of 2,4-pentanedione followed by 5.0 g of benzyl chloride. The solution was stirred over night at room temperature. 200ml of 1 molar hydrochloric acid was added and the solution was extracted with dichloromethane. The extract was washed 3 times with water and the solvent was evaporated in vacuo. The residue was distilled. Yield 2.9 g, bp 150°-154° C./15 mm.

Workup

  1. extractionthe solution was extracted with dichloromethane
  2. washThe extract was washed 3 times with water
  3. customthe solvent was evaporated in vacuo
  4. distillationThe residue was distilled

Sources & evidence

ORD record
ord-22b23c25e1a04d079c70cae51a2c8898
Source dataset
uspto-grants-1994_02
Patent number
US05288750

Reaction notes

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