Benzaldehyde → Flavanone

HRID 1408763Notes

Reaction equation

HRID 1408763 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:10])[CH3:9].[CH:11](=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(O)C.O>[C:12]1([CH:11]2[CH2:9][C:8](=[O:10])[C:3]3[C:2](=[CH:7][CH:6]=[CH:5][CH:4]=3)[O:1]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 240BenzaldehydeHCID 83752'-Hydroxyacetophenone

Product 1

HCID 10251FlavanoneYield 40.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A mixture of 1-(2-hydroxyphenyl)ethanone (30 g, 220 mmol), benzaldehyde (23.3 g, 220 mmol) and borax (84 g, 220 mmol) in ethanol (180 mL) and H2O (300 mL) was refluxed for one day. The reaction mixture was cooled, diluted with an equal volume of H2O, and extracted with ether. The combined organic layers were dried over anhydrous Na2SO4, filtered, and evaporated. The residue was purified by column to give 2-phenylchroman-4-one (20 g, 40%).

Workup

  1. temperaturewas refluxed for one day
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with ether
  4. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column

Sources & evidence

ORD record
ord-294c882aeb6a4dc3b711a60ac8230e98
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

Loading…