Phenylacetone → HCID 13670889, compound

HRID 414229Notes

Reaction equation

HRID 414229 reaction equation
[CH2:1]([O:8][C:9]1[CH:22]=[CH:21][CH:20]=[CH:19][C:10]=1[CH:11]=[C:12]([N+:16]([O-:18])=[O:17])[C:13](=O)[CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]1([CH2:29][C:30](=O)[CH3:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C([O-])(=O)C.[NH4+:37]>C(O)C>[CH2:1]([O:8][C:9]1[CH:22]=[CH:21][CH:20]=[CH:19][C:10]=1[CH:11]1[C:29]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:30]([CH3:31])[NH:37][C:13]([CH3:14])=[C:12]1[N+:16]([O-:18])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7678PhenylacetoneHCID 517165Ammonium AcetateHCID 54365084HCID 54365084, compound

Product 1

HCID 13670889HCID 13670889, compoundYield 4.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3 g (10 mmol) of 2-benzyloxybenzylidenenitroacetone in 15 ml of ethanol are heated under reflux with 1.34 g (10 mmol) of phenylacetone and 770 mg (10 mmol) of ammonium acetate for 1.5 hours. The mixture is cooled and concentrated. The residue from evaporation is taken up in ethyl acetate, and the solution is washed with water, dried and concentrated. The resulting residue from evaporation is purified through a column of volume 150 ml, stationary phase silica gel and mobile phase toluene/ethyl acetate 10:1. The pure fractions are combined, concentrated and crystallized using ether. 0.2 g of yellow crystals, of melting point 189° C., is obtained.

Workup

  1. temperatureThe mixture is cooled
  2. concentrationconcentrated
  3. customThe residue from evaporation
  4. washthe solution is washed with water
  5. customdried
  6. concentrationconcentrated
  7. customThe resulting residue from evaporation
  8. customis purified through a column of volume 150 ml, stationary phase silica gel and mobile phase toluene/ethyl acetate 10:1
  9. concentrationconcentrated
  10. customcrystallized

Sources & evidence

ORD record
ord-295368fdae204d59b40f418259a4b211
Source dataset
uspto-grants-1988_12
Patent number
US04791122

Reaction notes

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