Silica → 5-(Benzyloxy)pentanal

HRID 1090459Notes

Reaction equation

HRID 1090459 reaction equation
[C:1]1([CH2:7][O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][OH:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Si](=O)=O.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[Si]([O-])([O-])([O-])[O-].[Mg+2].[Mg+2]>C(Cl)Cl.C(OCC)C>[C:1]1([CH2:7][O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 24261SilicaHCID 66225Magnesium orthosilicateHCID 2211945-(Benzyloxy)pentan-1-olHCID 178418287HCID 178418287, compound

Product 1

HCID 110632585-(Benzyloxy)pentanalYield 78.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Under a nitrogen atmosphere a mixture of 8.0 grams (0.041 mole) of 7-phenyl-6-oxaheptan-1-ol and 1.4 grams of 95% silicon dioxide in 125 ml of methylene chloride was stirred, and 19.8 grams (0.090 mole) of pyridinium chlorochromate was added. Upon completion of addition, the reaction mixture was stirred at ambient temperature for four hours. After this time the reaction mixture was diluted with diethyl ether and then was passed through a column of magnesium silicate. The eluate was concentrated under reduced pressure yielding 6.2 grams of 7-phenyl-6-oxaheptan-1-al. The reaction was repeated.

Workup

  1. additionUpon completion of addition
  2. stirringthe reaction mixture was stirred at ambient temperature for four hours
  3. concentrationThe eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-520dbc8b40a94caab5f42feba8bec5b3
Source dataset
uspto-grants-1992_01
Patent number
US05081287

Reaction notes

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