Veratryl alcohol → Veratryl chloride

HRID 339649

Reaktionsgleichung

Reaktionsgleichung von HRID 339649
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH2:6]O.S(Cl)([Cl:15])=O>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH2:6][Cl:15]

Komponenten

4

Edukt 2

HCID 7118Veratryl alcoholHCID 24386Thionyl Chloride

Produkt 1

HCID 81740Veratryl chloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

3,4-dimethoxybenzyl alcohol (20 g, 119 mmol) was dissolved in toluene (60 ml) and cooled to 0° C. Thionyl chloride (7.48 g, 61.4 mmol) was added dropwise to the cooled solution of the alcohol over a period of 30 minutes, and the reaction was maintained at 0° C. for an additional 30 minutes. The reaction was quenched by pouring onto an ice/water mix (100 ml), and the organic phase was separated. The aqueous phase was then extracted into toluene (2×20 ml) and the combined toluene solution was dried over anhydrous sodium sulfate. The toluene was removed at reduced pressure to afford an oil which solidified upon standing, with a yield of 21 g. The material was characterized as a single spot by thin layer chromatography (TLC).

Aufarbeitung

  1. temperaturethe reaction was maintained at 0° C. for an additional 30 minutes
  2. customThe reaction was quenched
  3. additionby pouring onto an ice/water
  4. additionmix (100 ml)
  5. customthe organic phase was separated
  6. extractionThe aqueous phase was then extracted into toluene (2×20 ml)
  7. dry with materialthe combined toluene solution was dried over anhydrous sodium sulfate
  8. customThe toluene was removed at reduced pressure
  9. customto afford an oil which

Quellen und Nachweise

ORD-Eintrag
ord-182dff26fd8a47de90ddcafc14b88847
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895554B2

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