Diethyl Ether → HCID 178444538, compound

HRID 2166810Notes

Reaction equation

HRID 2166810 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(Cl)Cl.CC[O:17][CH2:18][CH3:19]>>[CH2:7]([C@H:9]1[CH2:10][CH2:11][C@H:19]([CH:18]=[O:17])[CH2:7][CH2:8]1)[CH2:8][CH2:9][CH2:10][CH3:11]

Participants

4

Reactant 3

HCID 3283Diethyl Ether2×HCID 6344DichloromethaneHCID 178418287HCID 178418287, compound

Product 1

HCID 178444538HCID 178444538, compound

Procedure

A solution of 59.0 g. of trans-4-n-pentylcyclohexane carbinol in 100 ml. of ether is added to a suspension of 125 g. of pyridinium chlorochromate in 900 ml. of methylene chloride and the mixture is stirred at room temperature for 2 hours. The mixture is then diluted with 400 ml. of ether, stirred for a further 15 minutes and the solution is decanted off from the tarry precipitate. The precipitate is back-washed with ether. The combined organic solutions are filtered through a Florisil column. The trans-4-n-pentylcyclohexane carboxaldehyde obtained after evaporation of the filtrate is used directly in the next step.

Workup

  1. additionThe mixture is then diluted with 400 ml
  2. customthe solution is decanted off from the tarry precipitate
  3. washThe precipitate is back-washed with ether
  4. filtrationThe combined organic solutions are filtered through a Florisil column

Sources & evidence

ORD record
ord-72455443b3df4a2496bf1029c92618fc
Source dataset
uspto-grants-1983_06
Patent number
US04389329

Reaction notes

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