2-(Oxan-2-yl)ethan-1-ol → 2-(Oxan-2-yl)acetaldehyde

HRID 1515734Notes

Reaction equation

HRID 1515734 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH2:7][CH2:8][OH:9].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH2:7][CH:8]=[O:9]

Participants

4

Reactant 2

HCID 139481282-(Oxan-2-yl)ethan-1-olHCID 178418287HCID 178418287, compound

Product 1

HCID 537991492-(Oxan-2-yl)acetaldehydeYield 72.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(tetrahydro-pyran-2-yl)-ethanol (53.5 g, 0.41 mol) in dichloromethane (1 L) was added pyridinium chlorochromate (176.8 g, 0.82 mol) in small portions at room temperature. The dark suspension was stirred for 3 h. The mixture was filtered through a short pad of silica gel. The filtrate was concentrated in vacuo and the residue was diluted with n-hexane (400 mL). The mixture was filtered through a short pad of silica gel and the filtrate was concentrated in vacuo to afford (tetrahydro-pyran-2-yl)-acetaldehyde (38 g) as a colorless oil.

Workup

  1. filtrationThe mixture was filtered through a short pad of silica gel
  2. concentrationThe filtrate was concentrated in vacuo
  3. additionthe residue was diluted with n-hexane (400 mL)
  4. filtrationThe mixture was filtered through a short pad of silica gel
  5. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-c134bd61477c4c6aa10e66fb65f859c9
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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