3-(cyclohexyloxy)propan-1-ol → HCID 22279671, compound

HRID 1063469Notes

Reaction equation

HRID 1063469 reaction equation
[CH:1]1([O:7][CH2:8][CH2:9][CH2:10][OH:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl.CCOCC>[CH:1]1([O:7][CH2:8][CH2:9][CH:10]=[O:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 100348783-(cyclohexyloxy)propan-1-olHCID 178418287HCID 178418287, compound

Product 1

HCID 22279671HCID 22279671, compoundYield 75.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

The obtained 3-cyclohexyloxypropan-1-ol (11.5 g, 72.9 mmol) was dissolved in dichloromethane (240 ml), and then molecular sieve 4 Å (58 g) and pyridinium chlorochromate (23.8 g, 0.11 mol) were added thereto in the ice bath followed by stirring under a nitrogen atmosphere for 1 hour and 40 minutes. The reaction solution was diluted with ether, and then the solution was filtered through Celite. The Celite was washed with diethyl ether, and this filtrate was added to the previous filtrate. The total filtrate was evaporated in vacuo, and the residue was purified roughly by chromatography on a silica gel column (elution solvent; n-hexane:ethyl acetate=20:1-10:1) to give a crude 3-cyclohexyloxypropionaldehyde (8.6 g).

Workup

  1. filtrationthe solution was filtered through Celite
  2. washThe Celite was washed with diethyl ether
  3. additionthis filtrate was added to the previous filtrate
  4. customThe total filtrate was evaporated in vacuo
  5. customthe residue was purified roughly by chromatography on a silica gel column (elution solvent; n-hexane:ethyl acetate=20:1-10:1)

Sources & evidence

ORD record
ord-8dae63e5e5a747458a25a77ee2fd048f
Source dataset
uspto-grants-2005_11
Patent number
US06964976B2

Reaction notes

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