2-(Oxan-4-yl)ethan-1-ol → 2-(Oxan-4-yl)acetaldehyde

HRID 1515756Notes

Reaction equation

HRID 1515756 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][OH:9])[CH2:3][CH2:2]1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH:8]=[O:9])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 177509442-(Oxan-4-yl)ethan-1-olHCID 178418287HCID 178418287, compound

Product 1

HCID 177509432-(Oxan-4-yl)acetaldehydeYield 50.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(tetrahydro-pyran-4-yl)-ethanol (13 g, 0.1 mol) in dichloromethane (150 mL) was added pyridinium chlorochromate (43 g, 0.2 mol) portion-wise at room temperature. The dark suspension was stirred at room temperature for 5 h. The reaction mixture was filtered through a short pad of silica gel. The filtrate was concentrated in vacuo to afford (tetrahydro-pyran-4-yl)-acetaldehyde (6.5 g, 50%) as a yellow oil which was used in the next step without purification.

Workup

  1. filtrationThe reaction mixture was filtered through a short pad of silica gel
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-e0db19873e8a49f8879602fbd318343e
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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