Phenylacetone → HCID 53868809, compound

HRID 497294Notes

Reaction equation

HRID 497294 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-2fbd368b1e7545b58a2e245e57aae5bb
Source dataset
uspto-grants-2005_09
Patent number
US06949536B2

Reaction notes

Loading…