Benzaldehyde → 1-(2,6-Dimethoxyphenyl)-3-phenylprop-2-en-1-one

HRID 990900

Reaktionsgleichung

Reaktionsgleichung von HRID 990900
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][C:10]([C:12]1[C:17]([O:18][CH3:19])=[CH:16][CH:15]=[CH:14][C:13]=1[O:20][CH3:21])=[O:11].[OH-].[Na+]>CO.O>[CH3:21][O:20][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]([O:18][CH3:19])[C:12]=1[C:10](=[O:11])[CH:9]=[CH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 240BenzaldehydeHCID 14798Sodium HydroxideHCID 162671-(2,6-Dimethoxyphenyl)ethanone

Produkt 1

HCID 2274471-(2,6-Dimethoxyphenyl)-3-phenylprop-2-en-1-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

(38) To a solution of benzaldehyde (295 mg, 2.77 mmol) and 2,6-dimethoxyacetophenone (500 mg, 2.77 mmol) in 4.1 ml of methanol was added 0.1 ml of 40% sodium hydroxide in water at 10° C. After stirring for 3 hour at room temperature, a solid appeared and was filtered. The precipitate was recrystallized from methanol to afford 371 mg (49.9%) of white flakes: mp 125.5-126.6° C. (lit. mp 123-124° C., Kuck and Grutzmacher, Org. Mass. Spect., 1978, 13, 90-102). 1H NMR (250 MHz) δ 7.55-7.51 (m, 2H), 7.39-7.30 (m, 5H), 7.00-6.94 (d, 1H), 6.64-6.61 (d, 2H), 3.79 (s, 6H); 13C NMR (62.7 MHz) 231.8, 176.1, 163.9, 153.4, 149.4, 149.0, 147.4, 147.3, 147.0, 122.6, 74.5 ppm.

Aufarbeitung

  1. filtrationwas filtered
  2. customThe precipitate was recrystallized from methanol
  3. customto afford 371 mg (49.9%) of white flakes

Quellen und Nachweise

ORD-Eintrag
ord-779d43c9b2514ece9a0798feab20cf77
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06462075B1

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