Sodium Hydroxide → (e)-1-(3-Hydroxy-4-propoxyphenyl)-3-(3,5-dimethoxyphenyl)prop-1-en-3-one

HRID 2217063노트

반응식

HRID 2217063 반응식
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH2:12][CH3:13])[CH:5]=O.[CH3:14][C:15]([C:17]1[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[C:19]([O:25][CH3:26])[CH:18]=1)=[O:16].[OH-].[Na+]>CO>[OH:1][C:2]1[CH:3]=[C:4](/[CH:5]=[CH:14]/[C:15]([C:17]2[CH:18]=[C:19]([O:25][CH3:26])[CH:20]=[C:21]([O:23][CH3:24])[CH:22]=2)=[O:16])[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH2:12][CH3:13]

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 959971-(3,5-Dimethoxyphenyl)ethan-1-oneHCID 219461763-Hydroxy-4-propoxybenzaldehyde

생성물 1

HCID 9967877(e)-1-(3-Hydroxy-4-propoxyphenyl)-3-(3,5-dimethoxyphenyl)prop-1-en-3-one수율 132.1%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A mixture of 3-hydroxy-4-propoxybenzaldehyde (0.4 g, 2.1 mmol), 3,5-dimethoxyacetophenone (0.371 mg, 2.1 mmol) and 50% w/v of aqueous sodium hydroxide (3.3 ml, 0.206 mol) in methanol (10 ml) at room temperature for 18 h. The yellow solid that precipitated was filtered and sequentially washed with cold methanol and ether and finally dried in a vacuum dessicator. Purification was achieved using column chromatography (SiO2, petroleum:ether (40:60 v/v) with an increasing gradient of ethyl acetate) which gave 0.95 g (19%) of a yellow solid. 1H-NMR (CDCl3) δ 7.7 (d, 1H), 7.3 (m, 2H), 7.1 (d, 3H), 6.8 (d, 1H), 6.6 (d, 1H), 5.7 (s, 1H), 4.1 (t, 2H), 3.9 (s, 6H), 1.9 (m, 2H), 1.0 (t, 3H). 13C-NMR (CDCl3) δ 160.9, 146.0, 144.9, 128.4, 122.6, 120.2, 112.9, 106.2, 104.9, 70.6, 55.6, 22.4, 10.4. Mass Spectrum m/e (M+1) 343. Anal. Calcd. for C20H22O5: C, 70.16; H, 6.48. Found C, 70.08; H, 6.38.

후처리

  1. filtrationThe yellow solid that precipitated was filtered
  2. washsequentially washed with cold methanol and ether
  3. customfinally dried in a vacuum dessicator
  4. customPurification

출처 및 근거

ORD 기록
ord-9dab6cf371a745b1883ada18bafbe116
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07112698B2

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