Ethanol → 3'-Cyano flavanone

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

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.