Phenylacetone → HCID 53868809, compound

HRID 396851Notes

Reaction equation

HRID 396851 reaction equation
[C:1]1([CH2:7][C:8](=[O:10])[CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1.N1CCCCC1>C1C=CC=CC=1>[Br:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:8](=[O:10])[CH3:9])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 7678PhenylacetoneHCID 8082PiperidineHCID 707414-Bromobenzaldehyde

Product 1

HCID 53868809HCID 53868809, compoundYield 38.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of phenylacetone (4.92 g, 36.7 mmol) and 4-bromobenzaldehyde (6.78 g, 36.7 mmol) in benzene (40 ml) in the presence of piperidine (0.11 ml, 1.47 mmol) was refluxed for 48 hours. After evaporation, the obtained residue was chromatographed on a column of silica gel (300 g) as eluting with ethyl acetate/hexane (1:20 to 1:2) to afford a yellow solid, which was washed with ethyl acetate/hexane to give 4.22 g (38%) of the title compound as a pale yellow solid.

Workup

  1. temperaturewas refluxed for 48 hours
  2. customAfter evaporation
  3. customthe obtained residue was chromatographed on a column of silica gel (300 g)
  4. washas eluting with ethyl acetate/hexane (1:20 to 1:2)
  5. customto afford a yellow solid, which
  6. washwas washed with ethyl acetate/hexane

Sources & evidence

ORD record
ord-6faa410391504068a1df1107c2cec8dc
Source dataset
uspto-grants-2003_08
Patent number
US06608095B2

Reaction notes

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