Ethyl Acetate → HCID 19791668, compound

HRID 236407Notes

Reaction equation

HRID 236407 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)pentane-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 being cooled, the reaction mixture was added with ethyl acetate (100 ml) and with 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 resulting crystals were recrystallized from hexane to obtain 12.2 g of the intended compound as white crystals (yield: 73%).

Workup

  1. temperatureAfter being cooled
  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 resulting crystals were recrystallized from hexane

Sources & evidence

ORD record
ord-0110718d0f334a0cadf34104694754a8
Source dataset
uspto-grants-1987_02
Patent number
US04644063

Reaction notes

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