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

HRID 262871Notes

Reaction equation

HRID 262871 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 give 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
  5. customto give an orange liquid, pmr spectrum (CDCl3)

Sources & evidence

ORD record
ord-aeaf092fbe2c40e6b4c8106abf8a4158
Source dataset
uspto-grants-1979_05
Patent number
US04154959

Reaction notes

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