Hydrochloric Acid → HCID 54328835, compound

HRID 742083Notes

Reaction equation

HRID 742083 reaction equation
[OH:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[CH3:11][CH:12]=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[OH-].[Na+].Cl.[CH2:23]([OH:25])C>O>[CH3:11][CH:12]=[CH:13][C:14]1[CH:19]=[CH:18][C:17]([C:23]2[O:25][C:10]3[C:5]([C:3](=[O:4])[C:2]=2[OH:1])=[CH:6][CH:7]=[CH:8][CH:9]=3)=[CH:16][CH:15]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 12500beta-MethylstyreneHCID 14798Sodium HydroxideHCID 68490alpha-Hydroxyacetophenone

Product 1

HCID 54328835HCID 54328835, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 4.92 g (36.1 mmol) of 2-hydroxyacetophenone, 3.30 g (34.2 mmol) of β-methyl styrene, 4-carboxaldehyde (mixture of cis and trans isomers) and 8.15 g NaOH (in 15 ml of water) in 125 ml of ethanol was stirred for 12 hours before the solution was poured into 600 ml of water. The resulting mixture was neutralized with dilute HCl. The yellow precipitate obtained was filtered and dried. The chalcone was purified by recrystallized from methylene chloride. Further oxidation of above chalcone was carried out with excess of H2O2 (30%) in ethanol under basic conditions for 12 hours. The resulting solution was poured into 300 ml water and acidified with dilute HCl. Yellow precipitate obtained was filtered and dried. 3-hydroxy-4'-(β-ethenyl) flavone was recrystallized from THF/hexane mixture. Yield: 35%. Quantum Yield: (1.75 relative to 3HF in methyl cyclohexane), Extinction coefficient: εmax (M-1 cm-1)=24000. λmax (abs)=355 nm and λmax (em)=551 nm.

Workup

  1. customThe yellow precipitate obtained
  2. filtrationwas filtered
  3. customdried
  4. customThe chalcone was purified
  5. customby recrystallized from methylene chloride
  6. customfor 12 hours
  7. additionThe resulting solution was poured into 300 ml water
  8. customYellow precipitate obtained
  9. filtrationwas filtered
  10. customdried
  11. custom3-hydroxy-4'-(β-ethenyl) flavone was recrystallized from THF/hexane mixture

Sources & evidence

ORD record
ord-5f21ded44d6f4a93a0e71e1268b5d7d3
Source dataset
uspto-grants-1996_09
Patent number
US05552551

Reaction notes

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