Homovanillyl alcohol → 4-Hydroxy-3-methoxyphenethyl chloride

HRID 21406

Reaktionsgleichung

Reaktionsgleichung von HRID 21406
S(Cl)([Cl:3])=O.[OH:5][C:6]1[CH:14]=[CH:13][C:9]([CH2:10][CH2:11]O)=[CH:8][C:7]=1[O:15][CH3:16]>ClCCl>[OH:5][C:6]1[CH:14]=[CH:13][C:9]([CH2:10][CH2:11][Cl:3])=[CH:8][C:7]=1[O:15][CH3:16]

Komponenten

4

Edukt 2

HCID 16928Homovanillyl alcoholHCID 24386Thionyl Chloride

Produkt 1

HCID 212240924-Hydroxy-3-methoxyphenethyl chloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Thionyl chloride (0.5 ml) was added, dropwise, to a! stirred solution of 4-hydroxy-3-methoxyphenethyl alcohol (0.83 g--commercially available) in dichloromethane (50 ml). When the addition was complete, the mixture was heated under reflux for 3 hours. On cooling to room temperature, the mixture was concentrated in vacuo to give a gum which was purified by column chromatography on silica eluting with dichloromethane containing methanol (0% up to 2%). The product-containing fractions were combined and concentrated in vacuo to give the title compound as an oil, yield 0.36 g.

Aufarbeitung

  1. additionWhen the addition
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 3 hours
  4. concentrationthe mixture was concentrated in vacuo
  5. customto give a gum which
  6. customwas purified by column chromatography on silica eluting with dichloromethane
  7. additioncontaining methanol (0% up to 2%)
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-124c450056884168846253c87de29ffb
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05422358

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