Sodium Iodide → HCID 12870379, compound

HRID 127802Notes

Reaction equation

HRID 127802 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-b5275fbb1143414693586d376710bc42
Source dataset
uspto-grants-1981_03
Patent number
US04256757

Reaction notes

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