Reaktion #55180

ord-33adb9ea9eaf4650a352ffb45849f2e3

Reaktionsgleichung

I
hydriodic acid
CCOC(=O)CC(C)(O)c1ccc(-c2ccc(F)cc2F)cc1
3-(2',4'-difluoro-4-biphenylyl)-3-hydroxybutyric acid ethyl ester
CC(=CC(=O)O)c1ccc(-c2ccc(F)cc2F)cc1
3-(2',4'-difluoro-4-biphenylyl)-2-butenoic acid
O=S([O-])O.[Na+]
NaHSO3
→
CC(CC(=O)O)c1ccc(-c2ccc(F)cc2F)cc1
3-(2',4'-difluoro-4-biphenylyl)butyric acid

Edukte

I
hydriodic acid
—
hydroxy acid
CCOC(=O)CC(C)(O)c1ccc(-c2ccc(F)cc2F)cc1
3-(2',4'-difluoro-4-biphenylyl)-3-hydroxybutyric acid ethyl ester
CC(=CC(=O)O)c1ccc(-c2ccc(F)cc2F)cc1
3-(2',4'-difluoro-4-biphenylyl)-2-butenoic acid
O=S([O-])O.[Na+]
NaHSO3

Reagenzien

Keine

Lösungsmittel

CC(=O)O
acetic acid

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.ADDITIONthe mixture is poured onto ice

Vorschrift

1 g. of 3-(2',4'-difluoro-4-biphenylyl)-3-hydroxybutyric acid ethyl ester, or the corresponding free hydroxy acid or 3-(2',4'-difluoro-4-biphenylyl)-2-butenoic acid, is heated with 2 ml. of 67% hydriodic acid and 4 ml. of acetic acid at 150° for 1 hour and the mixture is poured onto ice and decolorized with NaHSO3 solution. After the customary work up, 3-(2',4'-difluoro-4-biphenylyl)butyric acid, m.p. 109°-110°, is obtained.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04151302uspto-grants-1979_04