Benzene → HCID 11413365, compound

HRID 1614760Notes

Reaction equation

HRID 1614760 reaction equation
[C:1]([O-:4])(=O)[CH3:2].[C:5]([O-:8])(=O)C.[C:9]([O-])(=O)[CH3:10].[C:13]([O-])(=O)[CH3:14].[Pb+4].[C:18](=O)([O-])[O-].[K+].[K+].[CH:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CCCCCC>[CH2:18]([O:4][CH:1]([CH2:2][CH2:13][CH2:14][CH2:9][CH3:10])[CH:5]=[O:8])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 241BenzeneHCID 11430Potassium CarbonateHCID 178418268HCID 178418268, compound

Product 1

HCID 11413365HCID 11413365, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

After 260 mg of lead tetraacetate was added at 4° C. to a mixture of 200 mg of the diol [27] described above, 60 mg of potassium carbonate and 4.5 ml of anhydrous benzene, the mixture was stirred for 3 minutes. After completion of the reaction, 100 ml of hexane was added to the reaction solution. The reaction solution was filtered through Celite 545 and the filtrate was washed with saturated sodium bicarbonate aqueous solution. The aqueous phase was extracted with hexane twice. The extracts were combined and washed with saturated sodium chloride aqueous solution. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl ether:hexane=1:2 (volume)) to give 160 mg (yield, 80%) of (S) 2-benzyloxyheptanal [2].

Workup

  1. additionwas added to the reaction solution
  2. filtrationThe reaction solution was filtered through Celite 545
  3. washthe filtrate was washed with saturated sodium bicarbonate aqueous solution
  4. extractionThe aqueous phase was extracted with hexane twice
  5. washwashed with saturated sodium chloride aqueous solution
  6. dry with materialAfter drying over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (ethyl ether:hexane=1:2 (volume))
  9. customto give

Sources & evidence

ORD record
ord-7311a4e8e5264a3bb75f6dcc2bafb59f
Source dataset
uspto-grants-1993_03
Patent number
US05198588

Reaction notes

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