3-Methoxybenzaldehyde → HCID 58423788, compound

HRID 1408641Notes

Reaction equation

HRID 1408641 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH:17]=O>C(O)C.O>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[O:11][CH:17]([C:16]1[CH:19]=[CH:20][CH:21]=[C:14]([O:13][CH3:12])[CH:15]=1)[CH2:9][C:8]2=[O:10]

Participants

5

Reactant 2

HCID 115693-MethoxybenzaldehydeHCID 959915'-Bromo-2'-hydroxyacetophenone

Product 1

HCID 58423788HCID 58423788, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A mixture of 1-(5-bromo-2-hydroxy-phenyl)-ethanone (18 g, 84.1 mmol), 3-methoxy-benzaldehyde (11.4 g, 84.1 mol), and borax (51.5 g, 0.135 mol) in ethanol (112 mL) and H2O (187 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-bromo-2-(3-methoxy-phenyl)-chroman-4-one (5 g, 18%). 1H-NMR (CDCl3): 2.89 (d, 1H), 3.04 (t, 1H), 3.81 (s, 3H), 5.43 (d, 2H), 6.96 (m, 3H), 7.32 (m, 1H), 7.58 (m, 1H), 8.01 (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-2b442c2c09734e26a67d20e2fd381921
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

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