Sodium Acetate → 4-Oxo-1-iodo-trans-1-octene

HRID 66404Notes

Reaction equation

HRID 66404 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.C([O-])(=O)C.[Na+].[OH:17][CH:18]([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:19]/[CH:20]=[CH:21]/[I:22]>C(Cl)Cl.CCOCC>[O:17]=[C:18]([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:19]/[CH:20]=[CH:21]/[I:22]

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 128512784-Hydroxy-1-iodo trans-1-octeneHCID 178418287HCID 178418287, compound

Product 1

HCID 128512804-Oxo-1-iodo-trans-1-octene

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred suspension of 6.15 g of pyridinium chlorochromate (Tetrahedron Letters, 1975, 2647) in 20 ml of methylene chloride is added 450 mg of sodium acetate. After 5 minutes a solution of 3.64 g of 4-hydroxy-1-iodo-trans-1-octene in 15 ml of methylene chloride is added in one portion. The dark mixture is stirred at room temperature for 75 minutes, diluted with 50 ml of ether, and decanted. The solid sludge is washed repeatedly with ether and decanted. The combined solutions are percolated through Florisil. The solution is concentrated to given an orange liquid, pmr spectrum (CDCl3): 3.20 (d, j = 7 cps, =CHCH2CO).

Workup

  1. customdecanted
  2. washThe solid sludge is washed repeatedly with ether
  3. customdecanted
  4. concentrationThe solution is concentrated

Sources & evidence

ORD record
ord-68eca472d9394a88a2d52e2ae26f6780
Source dataset
uspto-grants-1978_12
Patent number
US04131737

Reaction notes

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