Réaction #417919

ord-2898d3da41d54f45b6bad8cd42ec1dc8

Équation de réaction

[O]=[Cr](=[O])([O-])[Cl].c1cc[nH+]cc1
PCC
CCCCCC/C=C\CCCOc1cccc(CO)c1
alcohol
CCCCCC/C=C\CCCOc1cccc(CO)c1
3-(undec-4Z-enyloxy)benzyl alcohol
CCCCCC/C=C\CCCOc1cccc(C=O)c1
yellow oil
Rendement 99.1%
CCCCCC/C=C\CCCOc1cccc(C=O)c1
3-(undec-4Z-enyloxy)benzaldehyde
Rendement 99.1%

Solvants

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Séchagedried by coevaporation with toluene
  2. 2
    TempératureThe reaction is heated to the reflux point of the DCM for 1 hour
  3. 3
    TempératureAfter cooling
  4. 4
    workup.ADDITIONthe reaction medium is diluted with ether
  5. 5
    Filtrationfiltered through Florisil
  6. 6
    ConcentrationAfter concentrating

Mode opératoire

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%.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US08877684B2uspto-grants-2014_11