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

HRID 1975625Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1975625
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[CH:11]([CH:13]=[CH2:14])[OH:12]>C(Cl)Cl.O=[Mn]=O>[CH:13]([C:11]([C:4]1[CH:5]=[C:6]([O:9][CH3:10])[CH:7]=[CH:8][C:3]=1[O:2][CH3:1])=[O:12])=[CH2:14]

Komponenten

4

Edukt 1

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

Produkt 1

HCID 127134602,5-Dimethoxyphenyl vinyl ketone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14801Manganese dioxideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Activated MnO2 (100 g) was added in portions to a mechanically stirred solution of 2,5-dimethoxyphenyl vinyl carbinol (12.5 g, 0.064 mole) in 250 ml of methylene chloride. The mixture was stirred at room temperature for 24 hours and then filtered through a patch of Celite. The filtrate was concentrated to give a brown oil which was purified by column chromatography on silica gel, using diethyl ether/hexane (1/1) as eluant. The compound was obtained as a light brown oil; 7.2 g; IR (neat) 1680 cm-1 ; NMR (CDCl3) δ6.85-7.1 (m,4H); 6.3 (d,1H); 5.8 (d,1H); 3.8 and 3.85 (two singlets,6H).

Aufarbeitung

  1. filtrationfiltered through a patch of Celite
  2. concentrationThe filtrate was concentrated
  3. customto give a brown oil which
  4. customwas purified by column chromatography on silica gel
  5. customThe compound was obtained as a light brown oil

Quellen und Nachweise

ORD-Eintrag
ord-20bd04e4cdea4128b511cc9f9c171dd1
Quelldatensatz
uspto-grants-1994_02
Patentnummer
US05288693

Notizen zur Reaktion

Wird geladen…