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

HRID 2217063Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2217063
[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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 9967877(e)-1-(3-Hydroxy-4-propoxyphenyl)-3-(3,5-dimethoxyphenyl)prop-1-en-3-oneAusbeute 132,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-9dab6cf371a745b1883ada18bafbe116
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07112698B2

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