3',4',5'-Trimethoxyacetophenone → (e)-1-(3-Hydroxy4-propoxyphenyl)-3-(3,4,5-trimethoxyphenyl)prop-1-en-3-one

HRID 2217072Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2217072
[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])[C:20]([O:25][CH3:26])=[C:19]([O:27][CH3:28])[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:27][CH3:28])[C:20]([O:25][CH3:26])=[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 143453',4',5'-TrimethoxyacetophenoneHCID 14798Sodium HydroxideHCID 219461763-Hydroxy-4-propoxybenzaldehyde

Produkt 1

HCID 10270608(e)-1-(3-Hydroxy4-propoxyphenyl)-3-(3,4,5-trimethoxyphenyl)prop-1-en-3-oneAusbeute 60,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 3-hydroxy-4-propoxybenzaldehyde (0.8 g, 4.4 mmol), 3,4,5-trimethoxyacetophenone (0.934 mg, 4.4 mmol) and 50% w/v of aqueous sodium hydroxide (7.0 ml, 0.089 mol) in methanol (10 ml) at room temperature for 18 h. The orange solid isolated by filtration was washed sequentially 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 0.995 g (60%) of a yellow solid. 1H-NMR (CDCl3) δ 7.7 (d, 1H), 7.2 (m, 4H), 7.1 (dd, 3H), 6.9 (d, 1H), 5.7 (s, 1H), 4.1 (t, 2H), 3.9 (s×2, 9H), 1.9 (m, 2H), 1.1 (t, 3H). 13C-NMR (CDCl3) δ 189.1, 153.1, 148.3, 146.0, 144.7, 142.4, 133.7, 128.4, 122.9, 119.8, 112.7, 111.4, 106.1, 70.6, 60.9, 56.4, 22.4, 10.4. Mass Spectrum m/e (M+1) 373. Anal. Calcd. for C21H24O6: C, 67.73; H, 6.5. Found C, 68.01; H, 6.72.

Aufarbeitung

  1. customThe orange solid isolated by filtration
  2. washwas washed sequentially with cold methanol and ether
  3. customfinally dried in a vacuum dessicator
  4. customPurification

Quellen und Nachweise

ORD-Eintrag
ord-32c933386d3a4cc599f6162ce5747f67
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07112698B2

Notizen zur Reaktion

Wird geladen…