Sodium Iodide → HCID 20197291, compound

HRID 1249014Notes

Reaction equation

HRID 1249014 reaction equation
Br[CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:16])[CH3:15])=[C:10]([OH:17])[C:9]=1[CH2:18][CH2:19][CH3:20].[C-:21]#[N:22].[Na+].[I-].[Na+]>CN(C)C=O>[C:14]([C:11]1[CH:12]=[CH:13][C:8]([O:7][CH2:6][CH2:5][O:4][CH2:3][CH2:2][C:21]#[N:22])=[C:9]([CH2:18][CH2:19][CH3:20])[C:10]=1[OH:17])(=[O:16])[CH3:15]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 8929Sodium CyanideHCID 21286972HCID 21286972, compound

Product 1

HCID 20197291HCID 20197291, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2.60 g of 1-[4-[2-(2-bromoethoxy)ethoxy]-2-hydroxy-3-propylphenyl]ethanone, 0.50 g of sodium cyanide and 1.13 g of sodium iodide in 50 ml of dimethyl formamide was stirred and heated at 80° for 6 hours. The solvent was removed in vacuo, water was added to the residue and the product was extracted with ether. The dried (over magnesium sulfate) extract was concentrated in vacuo to give 2.13 g of impure 3-[2-(4-acetyl-3-hydroxy-2-propylphenoxy)ethoxy]propanenitrile.

Workup

  1. temperatureheated at 80° for 6 hours
  2. customThe solvent was removed in vacuo, water
  3. additionwas added to the residue
  4. extractionthe product was extracted with ether
  5. dry with materialThe dried (over magnesium sulfate)
  6. extractionextract
  7. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-7cc6d04df02740c492ebaff1ae0009e5
Source dataset
uspto-grants-1986_12
Patent number
US04628115

Reaction notes

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