Water → 4-Oxo-1-iodo-trans-1-octene

HRID 126726

Reaction equation

HRID 126726 reaction equation
[OH:1][CH:2]([CH2:7][CH2:8][CH2:9][CH3:10])[CH2:3]/[CH:4]=[CH:5]/[I:6].O.O.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+].O.S(=O)(=O)(O)O>CCOCC>[I:6]/[CH:5]=[CH:4]/[CH2:3][C:2](=[O:1])[CH2:7][CH2:8][CH2:9][CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 108005Sodium dichromate dihydrateHCID 12851278HCID 12851278, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 6.4 g. of 4-hydroxy-1-iodo-trans-1-octene (U.S. Pat. No. 4,061,671, Ex. 4) in 25 ml. of ether, cooled in an ice-bath under argon, is added dropwise over 15 minutes, 25 ml. of a solution prepared by dissolving 100 g. of sodium dichromate dihydrate in 300 ml. of water, followed by 136 g. of sulfuric acid with ice-bath cooling and subsequent dilution to 500 ml. After addition, the mixture is stirred at room temperature for 2 hours and diluted with ether. The ether phase is separated and saved. The aqueous phase is extracted with ether. The ether solutions are combined, washed with saturated sodium chloride solution, 5% sodium thiosulfate solution, twice with saturated sodium chloride solution, dried over magnesium sulfate and taken to dryness, giving the product as an orange oil.

Workup

  1. additionis added dropwise over 15 minutes
  2. customof a solution prepared
  3. dissolutionby dissolving 100 g
  4. additionAfter addition
  5. customThe ether phase is separated
  6. extractionThe aqueous phase is extracted with ether
  7. washwashed with saturated sodium chloride solution, 5% sodium thiosulfate solution, twice with saturated sodium chloride solution
  8. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-9f27ed1469a7497aa4a2f184c9209746
Source dataset
uspto-grants-1981_03
Patent number
US04254036

Linked notes

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