Ethyl Acetate → HCID 19791668, compound

HRID 1655334Notes

Reaction equation

HRID 1655334 reaction equation
Br[CH:2]([CH2:12][CH:13]([CH3:15])[CH3:14])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=1)=[O:4].[C:16]1(=[O:26])[NH:20][C:19](=[O:21])[C:18]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:17]12.[K].C(OCC)(=O)C>O>[CH3:14][CH:13]([CH3:15])[CH2:12][CH:2]([N:20]1[C:16](=[O:26])[C:17]2[C:18](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:19]1=[O:21])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 197917002-Bromo-4-methyl-1-(4-methylphenyl)pentan-1-oneHCID 24194345Phthalimide potassium salt

Product 1

HCID 19791668HCID 19791668, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

2-Bromo-4-methyl-1-(4-methylphenyl)pentan-1-one (13.5 g, 50 mmol) and potassium phthalimide (9.26 g, 50 mmol) were thoroughly mixed and heated at 160° C. for 2 hours. After cooling, to the reaction mixture were added ethyl acetate (100 ml) and water (50 ml). The resulting organic layer was separated and washed with brine. The organic solution was then dried over sodium sulfate and evaporated under reduced pressure. The residue was crystallized by treatment with hexane and the crystals were recrystallized from hexane to obtain 12.2 g of the title compound as white crystals (yield: 73%).

Workup

  1. temperatureAfter cooling, to the reaction mixture
  2. customThe resulting organic layer was separated
  3. washwashed with brine
  4. dry with materialThe organic solution was then dried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue was crystallized by treatment with hexane
  7. customthe crystals were recrystallized from hexane

Sources & evidence

ORD record
ord-8555f444a1b946d698d57686d0c5980e
Source dataset
uspto-grants-1993_10
Patent number
US05250546

Reaction notes

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