Piperonal → 3'-Hydroxy-3,4-methylenedioxy chalcone

HRID 1157976

반응식

HRID 1157976 반응식
[CH3:1][C:2]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([OH:10])[CH:9]=1)=[O:3].[CH2:11]1[O:21][C:20]2[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][C:13]=2[O:12]1.[OH-].[Na+]>CO>[OH:10][C:8]1[CH:9]=[C:4]([CH:5]=[CH:6][CH:7]=1)[C:2](=[O:3])[CH:1]=[CH:16][C:15]1[CH:18]=[CH:19][C:20]2[O:21][CH2:11][O:12][C:13]=2[CH:14]=1

참가 물질

5

반응물 3

HCID 8438PiperonalHCID 84873-HydroxyacetophenoneHCID 14798Sodium Hydroxide

생성물 1

HCID 4662443'-Hydroxy-3,4-methylenedioxy chalcone

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

3-Hydroxy acetophenone, 2 (2.7 g, 20 mmol), 3,4-methylenedioxy benzaldehyde, 6 (3 g, 20 mmol) and 50% aqueous sodium hydroxide (5 mL) in methanol (40 mL) were reacted under reflux as in 7 to yield 12. Yield 4.1 g (76%); mp 188-189° C.; MS (FAB) 269 (M++1); IR (KBr) 3389, 1659; 1H NMR (300 MHz, DMSO-d6) δ 9.84 (s, 1H), 7.73 (d, J=15.6 Hz, 1H), 7.64 (d, J=15.9 Hz, 1H), 7.63 (s, 1H), 7.62 (d, J=5.4 Hz, 1H), 7.45 (s, 1H), 7.36 (t, J=7.9 Hz, 1H), 7.30 (d, J=7.8 Hz, 1H), 7.05 (dd, J=7.9 Hz, 2.4 Hz, 1H), 6.98 (d, J=7.8 Hz, 1H), 6.09 (s, 2H).

후처리

  1. temperatureunder reflux as in 7

출처 및 근거

ORD 기록
ord-2322ac7b9e8e405ab9a13def21c7a1bc
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07807712B2

연결된 노트

불러오는 중…