3-(Undec-4z-enyloxy)benzyl alcohol → 3-(Undec-4z-enyloxy)benzaldehyde

HRID 2091472Notes

Reaction equation

HRID 2091472 reaction equation
C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O.[CH2:12]([O:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[CH2:27][OH:28])[CH2:13][CH2:14]/[CH:15]=[CH:16]\[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>C(Cl)Cl>[CH2:12]([O:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[CH:27]=[O:28])[CH2:13][CH2:14]/[CH:15]=[CH:16]\[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

4

Reactant 2

HCID 579392363-(Undec-4z-enyloxy)benzyl alcoholHCID 178418287HCID 178418287, compound

Product 1

HCID 579391933-(Undec-4z-enyloxy)benzaldehydeYield 99.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10 mL of anhydrous DCM and then 190 mg of PCC (881 μmol) are added under argon to 120 mg of alcohol 16 (434 μmol) dried by coevaporation with toluene. The reaction is heated to the reflux point of the DCM for 1 hour. After cooling, the reaction medium is diluted with ether and filtered through Florisil. After concentrating, 118 mg of a yellow oil are obtained, i.e. a yield of 99%.

Workup

  1. dry with materialdried by coevaporation with toluene
  2. temperatureThe reaction is heated to the reflux point of the DCM for 1 hour
  3. temperatureAfter cooling
  4. additionthe reaction medium is diluted with ether
  5. filtrationfiltered through Florisil
  6. concentrationAfter concentrating

Sources & evidence

ORD record
ord-1d4832ba12c74cf7ad593c54575969a3
Source dataset
uspto-grants-2013_05
Patent number
US08440591B2

Reaction notes

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