2,5-Dimethoxybenzaldehyde → 1-(2,5-Dimethoxyphenyl)prop-2-en-1-ol

HRID 1975624Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1975624
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:4]=1[CH:5]=[O:6].[CH:13]([Mg]Br)=[CH2:14]>C1COCC1>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:4]=1[CH:5]([CH:13]=[CH2:14])[OH:6]

Komponenten

4

Edukt 2

HCID 667262,5-DimethoxybenzaldehydeHCID 178418507HCID 178418507, Verbindung

Produkt 1

HCID 190210221-(2,5-Dimethoxyphenyl)prop-2-en-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 2,5-dimethoxybenzaldehye (12.0 g, 0.072 mole) in 50 ml of dry THF was added dropwise to 100 ml of 1M solution of vinyl magnesium bromide in THF while keeping the reaction mixture at room temperature with cooling. The mixture was stirred for 4 hours at room temperature and then quenched with saturated NH4Cl solution. The layers were separated and the aqueous portion was extracted with diethyl ether. The combined organic portion was washed with water, dried (MgSO4), and concentrated. The resulting oil, 13.4 g, was sufficiently pure for the next reaction; IR (neat) 3500 cm-1); NMR (CDCl3) δ6.7-7.0 (m,3H); 6.0-6.2 (m, 1H); 5.1-5.3 (m,3H); 3.75 (two singlets, 6H); 3.16 (br,1H).

Aufarbeitung

  1. customat room temperature
  2. temperaturewith cooling
  3. customquenched with saturated NH4Cl solution
  4. customThe layers were separated
  5. extractionthe aqueous portion was extracted with diethyl ether
  6. washThe combined organic portion was washed with water
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customThe resulting oil, 13.4 g, was sufficiently pure for the next reaction

Quellen und Nachweise

ORD-Eintrag
ord-061c390896fa4c48b7d8a756078c0362
Quelldatensatz
uspto-grants-1994_02
Patentnummer
US05288693

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