Propionic Acid → HCID 18317670, compound

HRID 1700454Notes

Reaction equation

HRID 1700454 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:13][C:12](=[O:14])[CH2:11][C:10](=[O:15])[CH2:9]1.[C:16](O)(=[O:19])[CH2:17][CH3:18].CN(C1C=CC=CN=1)C.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:13][C:12](=[O:14])[CH:11]([C:16](=[O:19])[CH2:17][CH3:18])[C:10](=[O:15])[CH2:9]1

Participants

6

Reactant 4

HCID 1032Propionic AcidHCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 8753605-(2-Chlorophenyl)cyclohexane-1,3-dione

Product 1

HCID 18317670HCID 18317670, compoundYield 53.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-(2-chlorophenyl)cyclohexane-1,3-dione (1.0 g), propionic acid (0.60 g) and dimethylaminopyridine (0.82 g) in dimethylformamide (30 ml) was added dicyclohexylcarbodiimide (1.2 g), and the mixture was stirred at room temperature for 13 hours. Under reduced pressure, the solvent was evaporated, and to the residue was ethyl acetate. The mixture was washed with 1N hydrochloric acid and water, and to the mixture was added 1N sodium hydroxide solution. The aqueous layer was washed with diethylether, neutralized with 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure, and the residue was recrystallized from diisopropylether and hexane to give colorless crystals of 5-(2-chlorophenyl)-2-propionylcyclohexane-1,3-dione (0.67 g).

Workup

  1. customUnder reduced pressure, the solvent was evaporated
  2. washThe mixture was washed with 1N hydrochloric acid and water
  3. additionto the mixture was added 1N sodium hydroxide solution
  4. washThe aqueous layer was washed with diethylether
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with water and saturated brine
  7. dry with materialdried with magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customthe residue was recrystallized from diisopropylether and hexane

Sources & evidence

ORD record
ord-dcf274fda05c4686b3d31807e16cdb72
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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