Acetone → HCID 19847949, compound

HRID 568921Notes

Reaction equation

HRID 568921 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([CH2:11][CH2:12][CH3:13])[C:5]=1[OH:14])(=[O:3])[CH3:2].[C:15](=[O:18])([O-])[O-].[K+].[K+].[CH3:21][C:22]([CH3:24])=[O:23]>>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:8][CH2:7][CH2:6][CH2:11][CH2:12][O:23][C:22]2[CH:24]=[CH:4][CH:1]=[CH:2][C:21]=2[CH:15]=[O:18])=[C:6]([CH2:11][CH2:12][CH3:13])[C:5]=1[OH:14])(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 27751982',4'-Dihydroxy-3'-propylacetophenone

Product 1

HCID 19847949HCID 19847949, compound

Procedure

A solution of salicylaldehyde (82 mmoles) in acetone (50 ml) was added dropwise to a refluxing solution of 1,5-dibromopentane (90.2 mmoles), potassium carbonate (90.2 mmoles) and potassium iodide (0.4 g) in acetone (200 ml). The mixture was refluxed for 18 hours, filtered and the filtrate concentrated. The residue was dissolved in ether and washed with cold 10% sodium hydroxide solution, water and brine. The organic layer was dried over magnesiun sulfate and concentrated. The product was purified by flash chromatography (4% ethyl acetate/hexane) to give 2-(5-bromopentoxy)benzaldehyde. A mixture of this compound (11.1 mmoles), 4-acetyl-3-hydroxy-2-propyl phenol (11.62 mmoles) and potassium carbonate (5.55 mmoles) in acetone (30 ml) was refluxed for 5 days, stirred at room temperature for 2 days and then refluxed for 24 hours. The suspension was cooled to room temperature, filtered and the filtrate concentrated. The residue was dissolved in ethyl acetate and then washed with ice-cold 5% sodium hydroxide solution, water and brine. The dried solution was concentrated and the product flash chromatographed to give the desired product.

Workup

  1. temperaturewas refluxed for 5 days
  2. temperaturerefluxed for 24 hours
  3. temperatureThe suspension was cooled to room temperature
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated
  6. dissolutionThe residue was dissolved in ethyl acetate
  7. washwashed with ice-cold 5% sodium hydroxide solution, water and brine
  8. concentrationThe dried solution was concentrated
  9. customthe product flash chromatographed

Sources & evidence

ORD record
ord-a568f78547224d7eba4e4370b2e9d15f
Source dataset
uspto-grants-1988_03
Patent number
US04730005

Reaction notes

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