Hydrochloric Acid → 4-(2'-Hydroxy-3',4'-dimethoxy-6'-methylphenyl)butyric acid

HRID 1679844Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1679844
[OH:1][C:2]1[C:14]([O:15][CH3:16])=[C:13]([O:17][CH3:18])[CH:12]=[C:11]([CH3:19])[C:3]=1[C:4]([CH2:6][CH2:7][C:8]([OH:10])=[O:9])=O.Cl.O>C1(C)C=CC=CC=1>[OH:1][C:2]1[C:14]([O:15][CH3:16])=[C:13]([O:17][CH3:18])[CH:12]=[C:11]([CH3:19])[C:3]=1[CH2:4][CH2:6][CH2:7][C:8]([OH:10])=[O:9]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 129061353-(2'-Hydroxy-3',4'-dimethoxy-6'-methylbenzoyl)propionic acid

Produkt 1

HCID 129061404-(2'-Hydroxy-3',4'-dimethoxy-6'-methylphenyl)butyric acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 3-(2'-hydroxy-3',4'-dimethoxy-6'-methylbenzoyl)propionic acid (formula II-1 wherein R=H3CO, X=H, Y=OH, n=2 in the free form) (0.536 part), zinc amalgam (1 part), concentrated hydrochloric acid (1 volume part), water (2 volume parts) and toluene (2 volume parts) was refluxed for 5 hours and, after cooling, the reaction mixture was extracted with diethyl ether. The extract was washed with water and dried. The solvents were distilled off under reduced pressure and the residue was recrystallized from diethyl ether-hexane. The procedure provided 4-(2'-hydroxy-3',4'-dimethoxy-6'-methylphenyl)butyric acid (formula II-2 wherein R=H3CO, X=H, Y=OH, n=2, in the free form) (0.34 part) as colorless needles melting at 98°-100° C.

Aufarbeitung

  1. temperaturewas refluxed for 5 hours
  2. temperatureafter cooling
  3. extractionthe reaction mixture was extracted with diethyl ether
  4. washThe extract was washed with water
  5. customdried
  6. distillationThe solvents were distilled off under reduced pressure
  7. customthe residue was recrystallized from diethyl ether-hexane

Quellen und Nachweise

ORD-Eintrag
ord-af0429e446a24ccaa984859d30b17160
Quelldatensatz
uspto-grants-1981_06
Patentnummer
US04271083

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