Cornforth reagent → (8Z)-8-Tetradecenal

HRID 2055075Notes

Reaction equation

HRID 2055075 reaction equation
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[CH2:22]([OH:36])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]/[CH:29]=[CH:30]\[CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]>ClCCl>[CH:22](=[O:36])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]/[CH:29]=[CH:30]\[CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 6431341(Z)-8-Tetradecen-1-ol

Product 1

HCID 6430188(8Z)-8-Tetradecenal

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

15.8 g pyridinium dichromate in 300 ml dichloromethane were initially introduced under blanketing gas and 5.93 g (Z)-8-tetradecen-1-ol (5) in 50 ml dichloromethane was added, with stirring. The reaction mixture was stirred for 15 h at room temperature and filtered through silica gel. Distillation under a high vacuum gave (Z)-8-tetradecenal (6).

Workup

  1. additionwas added
  2. stirringThe reaction mixture was stirred for 15 h at room temperature
  3. filtrationfiltered through silica gel
  4. distillationDistillation under a high vacuum

Sources & evidence

ORD record
ord-28e4c21cc17248f598c7cdf0cfd08de9
Source dataset
uspto-grants-2008_02
Patent number
US07332468B2

Reaction notes

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