Hydrochloric Acid → Cinnamoylbenzene

HRID 742086

반응식

HRID 742086 반응식
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

참가 물질

7

반응물 4

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

생성물 1

HCID 7189Cinnamoylbenzene

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-84706179739d4368beb848e9b10a3d1c
출처 데이터셋
uspto-grants-1996_09
특허 번호
US05552551

연결된 노트

불러오는 중…