Sodium Hydroxide → (1R,2R)-2-(3,4-Difluorophenyl)cyclopropanecarboxylic acid

HRID 2060960

Reaktionsgleichung

Reaktionsgleichung von HRID 2060960
[OH-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([C@@H:11]2[CH2:13][C@H:12]2[C:14]([O:16]CC)=[O:15])[CH:7]=[CH:8][C:9]=1[F:10]>CO>[F:3][C:4]1[CH:5]=[C:6]([C@@H:11]2[CH2:13][C@H:12]2[C:14]([OH:16])=[O:15])[CH:7]=[CH:8][C:9]=1[F:10]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 57407735Ethyl (1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarboxylate

Produkt 1

HCID 9834218(1R,2R)-2-(3,4-Difluorophenyl)cyclopropanecarboxylic acidAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

Methanol (322.2 g) and 30% sodium hydroxide aqueous solution (65.5 g, 1.8 molar equivalents) were added to a solution of ethyl (1R,2R)-2-(3,4-difluorophenyl)-1-cyclopropanecarboxylate (48.2 wt % toluene solution, net 61.22 g, 270.6 mmol). The mixture was heated at 65° C. with stirring for 2 hours. The resultant mixture was concentrated under reduced pressure, then toluene and water were added to the concentrate. The mixture was acidified with 35% hydrochloric acid. The organic layer was separated and concentrated under reduced pressure. (1R,2R)-2-(3,4-difluorophenyl)-1-cyclopropanecarboxylic acid was obtained as resultant concentrate (net 52.55 g, yield: 98%).

Aufarbeitung

  1. concentrationThe resultant mixture was concentrated under reduced pressure
  2. additiontoluene and water were added to the concentrate
  3. customThe organic layer was separated
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-9bd0f1a9145c40d38a20971521fe1f11
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08278475B2

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