Acetone → HCID 19847949, compound

HRID 2351066Notes

Reaction equation

HRID 2351066 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 magnesium 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 on silica gel and eluted with ethylacetate/hexane 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 on silica gel
  10. washeluted with ethylacetate/hexane

Sources & evidence

ORD record
ord-4e4e68d09a6e496b9152598c0b69662f
Source dataset
uspto-grants-1989_10
Patent number
US04871771

Reaction notes

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