Sodium Hydroxide → 4-Cyclopropyl-2-ethyl-5-iodobenzoic acid

HRID 541370Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 541370
[CH:1]1([C:4]2[C:13]([I:14])=[CH:12][C:7]([C:8]([O:10]C)=[O:9])=[C:6]([CH2:15][CH3:16])[CH:5]=2)[CH2:3][CH2:2]1.[OH-].[Na+]>CO>[CH:1]1([C:4]2[C:13]([I:14])=[CH:12][C:7]([C:8]([OH:10])=[O:9])=[C:6]([CH2:15][CH3:16])[CH:5]=2)[CH2:2][CH2:3]1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 68288857Methyl 4-cyclopropyl-2-ethyl-5-iodobenzoate2×

Produkt 1

HCID 682889274-Cyclopropyl-2-ethyl-5-iodobenzoic acidAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of methyl 4-cyclopropyl-2-ethyl-5-iodobenzoate (compound 226.4, 2.50 g, 7.57 mmol, 1.00 equiv) in methanol (40 mL) was added aqueous sodium hydroxide (3.10 g, 77.5 mmol, 10.0 equiv, in 10 mL water). The resulting mixture was stirred for 15 h at 60° C. in an oil bath. After cooling to ambient temperature, the organic solvent was removed under reduced pressure and pH of the remaining aqueous layer was adjusted to 4 with hydrogen chloride (aq, 1 M). The solids were collected by filtration and dried in an oven under reduced pressure to yield 2.20 g (92%) of 4-cyclopropyl-2-ethyl-5-iodobenzoic acid as a white solid.

Aufarbeitung

  1. temperatureAfter cooling to ambient temperature
  2. customthe organic solvent was removed under reduced pressure and pH of the remaining aqueous layer
  3. filtrationThe solids were collected by filtration
  4. customdried in an oven under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-0e2b08c945114a4f9d74168d5d0673df
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08871790B2

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