Hydrochloric Acid → Cinnamoylbenzene

HRID 742086

Reaktionsgleichung

Reaktionsgleichung von HRID 742086
O[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:10])[CH3:9].[C:11]1([C:17](C2C=CC=CC=2)=CC=O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[OH-].[Na+].Cl>O.CO>[C:11]1([CH:17]=[CH:9][C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:2]=2)=[O:10])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 83752'-HydroxyacetophenoneHCID 14798Sodium HydroxideHCID 710273,3-Diphenylacrolein

Produkt 1

HCID 7189Cinnamoylbenzene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 1.81 g (13.3 mmol) of 2'-hydroxyacetophenone, 2.75 g (13.2 mmol) of β-phenylcinnamaldehyde, 2.64 g NaOH (in 10 mL of water) and 100 mL MeOH was stirred for 24 hours before the solution was poured into 1000 mL water. The resulting mixture was neutralized with dilute HCl and the yellow precipitate was collected by filtration. Recrystallization from MeOH gave a pure intermediate chalcone product. Further oxidation of the above chalcone was carried out with excess H2O2 (30%) in basic (NaOH aq.) MeOH solution for 18 hours. This solution was poured into water, and neutralized with dilute HCl. The resulting light yellow precipitate was collected by filtration and the pure desired product was obtained by recrystallization from MeOH with 28% overall yield. MP: 215°-216° C. Quantum yield (relative to 3-hydroxyflavone in CH2Cl2) 0.004. Extinction coefficient εmax (M-1 cm-1) 23,000. λmax (abs)=378 nm and λmax (em)=470 nm.

Aufarbeitung

  1. filtrationthe yellow precipitate was collected by filtration
  2. customRecrystallization from MeOH

Quellen und Nachweise

ORD-Eintrag
ord-84706179739d4368beb848e9b10a3d1c
Quelldatensatz
uspto-grants-1996_09
Patentnummer
US05552551

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