Acetic Acid → HCID 178467252, compound

HRID 1700447Notes

Reaction equation

HRID 1700447 reaction equation
[CH3:1][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:18])[CH3:17].CN(C1C=CC=CN=1)C.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[OH:18][C:16](=[C:11]1[C:10](=[O:15])[CH2:9][CH:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[CH3:1])[CH2:13][C:12]1=[O:14])[CH3:17]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 176065755-(2-Methylphenyl)cyclohexane-1,3-dione

Product 1

HCID 178467252HCID 178467252, compoundYield 62.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-(2-methylphenyl)cyclohexane-1,3-dione (1.0 g), acetic acid (0.27 g) and dimethylaminopyridine (0.60 g) in dimethylformamide (45 ml) was added dicyclohexylcarbodiimide (1.0 g), and the mixture was stirred at room temperature for 12 hours. Under reduced pressure, the solvent was evaporated, and to the residue was added ethyl acetate. The organic layer was washed with potassium hydrogensulfate aqueous solution, and insoluble materials were filtered, to which was added 1N sodium hydroxide solution. The aqueous layer was 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 to give, the residue was recrystallized from ethyl acetate-hexane to give colorless crystals of 2-(1-hydroxyethylidene)-5-(2-methylphenyl)cyclohexane-1,3-dione (0.69 g).

Workup

  1. customUnder reduced pressure, the solvent was evaporated
  2. additionto the residue was added ethyl acetate
  3. washThe organic layer was washed with potassium hydrogensulfate aqueous solution, and insoluble materials
  4. filtrationwere filtered, to which
  5. additionwas added 1N sodium hydroxide solution
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with water and saturated brine
  8. dry with materialdried with magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customto give
  11. customthe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-4c6ec1b9c1b949eaaa23420ad6d7997d
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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