1-Tetradecanol → Tetradecanal

HRID 1710171Notes

Reaction equation

HRID 1710171 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[CH2:12]([OH:26])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>C(Cl)Cl>[CH:12](=[O:26])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

4

Reactant 2

HCID 82091-TetradecanolHCID 178418287HCID 178418287, compound

Product 1

HCID 31291Tetradecanal

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

32.3 g (150 mmol) of pyridinium chlorochromate are suspended in 200 ml of anhydrous methylene chloride at room temperature, with vigorous stirring, and a solution of 21.4 g (100 mmol) of tetradecanol in 20 ml of anhydrous methylene chloride is added. This results in the reaction mixture boiling. The reaction is complete after 11/2 hours. The solution is decanted off from the solid which is washed with about 200 ml of dry diethyl ether. After filtration and evaporation of the solvent, chromatography is carried out on silica gel using petroleum ether (boiling point 35°-80° C.)/ethyl acetate 9:1. Yield: 18 g (84%).

Workup

  1. customThis results in the reaction mixture
  2. custom2 hours
  3. customThe solution is decanted off from the solid which
  4. washis washed with about 200 ml of dry diethyl ether
  5. filtrationAfter filtration and evaporation of the solvent, chromatography

Sources & evidence

ORD record
ord-68974ddd379b45529800bc96f01b3bff
Source dataset
uspto-grants-1990_08
Patent number
US04952683

Reaction notes

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