Water → HCID 13579264, compound

HRID 1589096Notes

Reaction equation

HRID 1589096 reaction equation
[H][H].[F:3][C:4]([F:15])([F:14])[C:5]1[CH:6]=[C:7]([CH2:11][C:12]#[N:13])[CH:8]=[CH:9][CH:10]=1.[CH3:16][O:17][CH2:18][C:19](OC)=[O:20].O>C(O)C>[F:3][C:4]([F:14])([F:15])[C:5]1[CH:6]=[C:7]([CH:11]([C:19](=[O:20])[CH2:18][O:17][CH3:16])[C:12]#[N:13])[CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 75360m-TrifluoromethylphenylacetonitrileHCID 80507Methyl methoxyacetateHCID 178418361HCID 178418361, compound

Product 1

HCID 13579264HCID 13579264, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In this example 5.6 grams of metallic sodium was added to 120 ml of anhydrous ethanol at room temperature under a nitrogen atmosphere resulting in the evolution of hydrogen. After evolution of hydrogen was completed a mixture containing 30 g of (3-trifluoromethylphenyl)-acetonitrile and 18.5 g of methyl methoxyacetate in anhydrous ethanol was added and the resulting mixture refluxed for 3 to 4 hours. The mixture was then added to 300 ml of water and extracted three times with petroleum ether. The remaining aqueous phase was acidified with aqueous 10% hydrochloric acid to about pH 1 and extracted three times with ethyl ether. The ethyl ether extracts were combined, washed twice with saturated aqueous sodium bicarbonate, dried over magnesium sulfate and concentrated by evaporation. The concentrate was evaporated under high vacuum affording an oil which was triturated with ethyl ether. This mixture was then filtered to remove solids and the filtrate evaporated under vacuum affording 36.9 g of the title compound as a brown solid.

Workup

  1. additionwas added
  2. temperaturethe resulting mixture refluxed for 3 to 4 hours
  3. extractionextracted three times with petroleum ether
  4. extractionextracted three times with ethyl ether
  5. washwashed twice with saturated aqueous sodium bicarbonate
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated by evaporation
  8. customThe concentrate was evaporated under high vacuum
  9. customaffording an oil which
  10. customwas triturated with ethyl ether
  11. filtrationThis mixture was then filtered
  12. customto remove solids
  13. customthe filtrate evaporated under vacuum

Sources & evidence

ORD record
ord-1f3e48770b244ce392a9578517f7047b
Source dataset
uspto-grants-1986_02
Patent number
US04568376

Reaction notes

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