Benzaldehyde → 6-Methylflavanone

HRID 1408670Notes

Reaction equation

HRID 1408670 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10].[CH:12](=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(O)C.O>[CH3:8][C:5]1[CH:4]=[C:3]2[C:2](=[CH:7][CH:6]=1)[O:1][CH:12]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:10][C:9]2=[O:11]

Participants

5

Reactant 2

HCID 240BenzaldehydeHCID 150682-Hydroxy-5-methylacetophenone

Product 1

HCID 5841096-MethylflavanoneYield 34%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A mixture of 1-(2-hydroxy-5-methyl-phenyl)-ethanone (15 g, 0.10 mol), benzaldehyde (10.6 g, 0.10 mol) and borax (38 g, 0.10 mol) in ethanol (90 mL) and H2O (150 mL) was refluxed for one day. The reaction mixture was cooled, diluted with an equal volume of H2O and extracted with ether. The ether was dried over anhydrous Na2SO4, filtered, and evaporated to give 6-methyl-2-phenyl-chroman-4-one (8.1 g, 34%). 1H-NMR (CDCl3): 2.32 (s, 3H), 2.86 (d, 1H), 3.06 (t, 1H), 5.44 (d, 1H), 6.96 (d, 1H), 7.38 (d, 1H), 7.44 (m, 5H), 7.71 (s, 1H).

Workup

  1. temperaturewas refluxed for one day
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with ether
  4. dry with materialThe ether was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-13bfb7c252824172afcdfce4d3510b25
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

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