p-Toluenesulfonic acid → 1-(2-Hydroxy-3,4-dimethoxyphenyl)-1-(2-hydroxyphenyl)cyclopropane

HRID 2165022Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2165022
COC[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[C:15]=2[O:24]COC)[CH2:13][CH2:12]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[OH:24][C:15]1[C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=[CH:19][C:14]=1[C:11]1([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[OH:4])[CH2:12][CH2:13]1

Komponenten

4

Edukt 2

HCID 6101p-Toluenesulfonic acidHCID 198126851-(2-Methoxymethoxyphenyl)-1-(3,4-dimethoxy-2-methoxymethoxyphenyl)cyclopropane

Produkt 1

HCID 198126861-(2-Hydroxy-3,4-dimethoxyphenyl)-1-(2-hydroxyphenyl)cyclopropaneAusbeute 99,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 1.16 g (3.1 mmol) of 1-(2-methoxymethoxyphenyl)-1-(3,4-dimethoxy-2-methoxymethoxyphenyl)cyclopropane and 80 mg (0.47 mmol) of p-toluenesulfonic acid in 26 ml of methanol was heated at reflux with stirring for 2 hours under an argon atmosphere. The mixture was concentrated to half by evaporation under reduced pressure and 40 ml of ether was added. The resulting solution was extracted with 30 ml of 5 percent aqueous sodium bicarbonate then 30 ml of water, dried over magnesium sulfate, and concentrated by evaporation under reduced pressure to obtain 880 mg of the title compound as a foamy oil. The proton NMR spectrum was consistent with the assigned structure.

Aufarbeitung

  1. temperatureat reflux
  2. concentrationThe mixture was concentrated to half by evaporation under reduced pressure and 40 ml of ether
  3. additionwas added
  4. extractionThe resulting solution was extracted with 30 ml of 5 percent aqueous sodium bicarbonate
  5. dry with material30 ml of water, dried over magnesium sulfate
  6. concentrationconcentrated by evaporation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-4bbef6afdcfe48df9e4809a175f8357e
Quelldatensatz
uspto-grants-1990_07
Patentnummer
US04938790

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