Cetyl Alcohol → Hexadecanal

HRID 1710172Notes

Reaction equation

HRID 1710172 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[CH2:12]([OH:28])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>ClCCl.CCOCC>[CH:12](=[O:28])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

5

Reactant 2

HCID 2682Cetyl AlcoholHCID 178418287HCID 178418287, compound

Product 1

HCID 984Hexadecanal

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

21.5 g (100 mmol) of pyridinium chlorochromate are suspended in 200 ml of anhydrous dichloromethane. 16 g (66 mmol) of hexadecanol in 50 ml of anhydrous dichloromethane are added dropwise. After 2 hours, the mixture is diluted with 300 ml of anhydrous ether, and the solution is decanted off from the black residue. The residue is washed three times with about 50 ml of anhydrous ether. The organic phases are combined and the ether is evaporated off to dryness. The residue is chromatographed on silica gel using petroleum ether/ethyl acetate 9:1. Yield: 15 g (95%), melting point 33°-34° C.

Workup

  1. customthe solution is decanted off from the black residue
  2. washThe residue is washed three times with about 50 ml of anhydrous ether
  3. customthe ether is evaporated off to dryness
  4. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-b5b23cfc08534bc1bd92450caf1aabb9
Source dataset
uspto-grants-1990_08
Patent number
US04952683

Reaction notes

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