Diethyl Ether → HCID 178444538, compound

HRID 1680557Notes

Reaction equation

HRID 1680557 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-c11b8a1508b64791b4dbb577ba4945fe
Source dataset
uspto-grants-1981_06
Patent number
US04273929

Reaction notes

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