Diethyl Ether → p-Cyclohexylbenzaldehyde

HRID 322701

Reaction equation

HRID 322701 reaction equation
C1OCCOCCOCCOCCOCCOC1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[CH:30]1([C:36]2[CH:43]=[CH:42][C:39]([CH2:40][OH:41])=[CH:38][CH:37]=2)[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1.CCOCC>C(Cl)(Cl)Cl>[CH:30]1([C:36]2[CH:37]=[CH:38][C:39]([CH:40]=[O:41])=[CH:42][CH:43]=2)[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 2855718-Crown-6HCID 22492024(4-Cyclohexylphenyl)methanolHCID 178418287HCID 178418287, compound

Product 1

HCID 119689p-Cyclohexylbenzaldehyde

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

18-Crown-6 (Aldrich; 4 molar eq.) and pyridinium chlorochromate (Aldrich; 4 molar eq.) were added together in chloroform and stirred for 20 minutes. 4-Cyclohexylbenzylalcohol (from Example D22 below; 1 molar eq.) was added and stirring continued for 3 hours. Ether was added and the mixture filtered through a plug of silica eluting with ether. The solvent was removed via rotary evaporation. The residue was dissolved in ether and washed with water. The organic layer was dried over Na2SO4, filtered, and concentrated.

Workup

  1. stirringstirring
  2. waitcontinued for 3 hours
  3. filtrationthe mixture filtered through a plug of silica eluting with ether
  4. customThe solvent was removed via rotary evaporation
  5. dissolutionThe residue was dissolved in ether
  6. washwashed with water
  7. dry with materialThe organic layer was dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-5ad106ae8a9c4a0dac0950bb599b797b
Source dataset
uspto-grants-2001_04
Patent number
US06211235B1

Linked notes

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