Ethanol → 3'-Cyano flavanone

HRID 1733290Notes

Reaction equation

HRID 1733290 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=[O:7])#[N:2].O[CH2:12][C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:14].C(O)C>O>[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]1[CH2:12][C:13](=[O:14])[C:15]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[O:7]1)#[N:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 68490alpha-HydroxyacetophenoneHCID 90670m-Formylbenzonitrile

Product 1

HCID 545536863'-Cyano flavanoneYield 10.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 3-cyanobenzaldehyde (25 g, 0.19 mol), 2-hydroxyacetophenone (25.9 g. 0.19 mol), 38.1 g (0.1 mol) of borax, 250 ml of ethanol, and 250 ml of H2O was refluxed for four days. When cool the reaction mixture was diluted with H2O and extracted with ethyl acetate. The ethyl acetate was dried over anhydrous Na2SO4, filtered, and evaporated to give a dark, tarry residue. The residue was chromatographed on 1 kg of silica gel, eluting with benzene. From this was isolated 5 g of 3'-cyano flavanone as an oil.

Workup

  1. temperaturewas refluxed for four days
  2. temperatureWhen cool the reaction mixture
  3. extractionextracted with ethyl acetate
  4. dry with materialThe ethyl acetate was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customto give a dark, tarry residue
  8. customThe residue was chromatographed on 1 kg of silica gel
  9. washeluting with benzene

Sources & evidence

ORD record
ord-f7bded1ec96347c5b60a216e95b4a2a1
Source dataset
uspto-grants-1980_12
Patent number
US04241069

Reaction notes

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