Sodium Iodide → HCID 12870379, compound

HRID 223673Notes

Reaction equation

HRID 223673 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]#[C:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]Br.[I-:13].[Na+]>CC(C)=O>[CH3:1][O:2][C:3](=[O:12])[C:4]#[C:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][I:13]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 13596438HCID 13596438, compound

Product 1

HCID 12870379HCID 12870379, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 4.05 g of 8-bromo-2-octynoic acid methyl ester (prepared as described hereafter) in 24 ml of acetone was added 3.9 g of sodium iodide, the mixture was refluxed with heating for one hour, and concentrated under reduced pressure. The residue was dissolved in water, extracted with diethyl ether, the extract was washed with a saturated aqueous solution of sodium chloride, dried over sodium sulphate and concentrated under reduced pressure to give 4.80 g of the title compound having the following physical characteristics:

Workup

  1. temperaturethe mixture was refluxed
  2. temperaturewith heating for one hour
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in water
  5. extractionextracted with diethyl ether
  6. washthe extract was washed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f35da9f2a1cd498cb631eb2a45f46073
Source dataset
uspto-grants-1982_10
Patent number
US04355170

Reaction notes

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