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Ethanol → Benzenebutanenitrile, beta-oxo-alpha-(3-(trifluoromethyl)phenyl)-

HRID 1589093
Notes
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Reaction equation

HRID 1589093 reaction equation
[Na].C(O)C.[F:5][C:6]([F:17])([F:16])[C:7]1[CH:8]=[C:9]([CH2:13][C:14]#[N:15])[CH:10]=[CH:11][CH:12]=1.[C:18]1([CH2:24][C:25](OCC)=[O:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O>[F:5][C:6]([F:16])([F:17])[C:7]1[CH:8]=[C:9]([CH:13]([C:25]([CH2:24][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:26])[C:14]#[N:15])[CH:10]=[CH:11][CH:12]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 702EthanolHCID 7590Ethyl phenylacetateHCID 75360m-TrifluoromethylphenylacetonitrileHCID 5360545Sodium2×

Product 1

HCID 106559Benzenebutanenitrile, beta-oxo-alpha-(3-(trifluoromethyl)phenyl)-Yield 73.5%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

In this example, 4.91 g of metallic sodium was added to 110 ml of anhydrous ethanol at room temperature and stirred until all of the sodium dissolved. A mixture containing 18.76 g of (3-trifluoromethylphenyl)acetonitrile and 21.73 g of ethyl phenylacetate was then added dropwise and the resulting mixture was stirred at reflux for about 18 hours. The mixture was then poured into 300 ml water and extracted three times with ethyl ether. The pH of the extracted aqueous layer was adjusted to a pH of about 1 with aqueous 10 wt. % hydrochloric acid and again extracted three times with ethyl ether. The organic layer was washed twice with saturated aqueous sodium bicarbonate, dried over magnesium sulfate and evaporated to dryness under vacuum affording 22.6 g of the title compound.

Workup

  1. dissolutiondissolved
  2. additionwas then added dropwise
  3. temperatureat reflux for about 18 hours
  4. extractionextracted three times with ethyl ether
  5. extractionagain extracted three times with ethyl ether
  6. washThe organic layer was washed twice with saturated aqueous sodium bicarbonate
  7. dry with materialdried over magnesium sulfate
  8. customevaporated to dryness under vacuum

Sources & evidence

ORD record
ord-49605d1b4eb54723b0e3d3e2e958f459
Source dataset
uspto-grants-1986_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04568376

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes