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

HRID 541345Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 541345
[CH:1]1([C:5]2[C:14]([I:15])=[CH:13][C:8]([C:9]([O:11]C)=[O:10])=[C:7]([CH2:16][CH3:17])[CH:6]=2)[CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>CO.O>[CH:1]1([C:5]2[C:14]([I:15])=[CH:13][C:8]([C:9]([OH:11])=[O:10])=[C:7]([CH2:16][CH3:17])[CH:6]=2)[CH2:2][CH2:3][CH2:4]1

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 68288985Methyl 4-cyclobutyl-2-ethyl-5-iodobenzoate2×

Produkt 1

HCID 682889094-Cyclobutyl-2-ethyl-5-iodobenzoic acidAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a round-bottom flask, was added a solution of methyl 4-cyclobutyl-2-ethyl-5-iodobenzoate (compound 181.4, 10.3 g, 30.0 mmol, 1.00 equiv) in methanol (100 mL). A solution of sodium hydroxide (3.60 g, 3.00 equiv) in water (10 mL) was added dropwise to the stirred reaction mixture. The resulting mixture was stirred for 2 h at 60° C. After cooling to ambient temperature, the volatiles were removed under reduced pressure. The pH of the remaining aqueous mixture was adjusted to ˜4 using HCl (aq., 1 M). The resulting precipitate was collected by filtration and dried to yield 9.00 g (91%) of 4-cyclobutyl-2-ethyl-5-iodobenzoic acid as a white solid.

Aufarbeitung

  1. temperatureAfter cooling to ambient temperature
  2. customthe volatiles were removed under reduced pressure
  3. filtrationThe resulting precipitate was collected by filtration
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-81ba5a0af4e243d9bfbd6f1bea331531
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08871790B2

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