Water → 2-(3-Chloro-4-cyanophenyl)propanoic acid

HRID 1428745Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1428745
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]([CH3:15])[C:11]([O:13]C)=[O:12])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].O1CCCC1.O.[OH-].[Na+]>C(OCC)(=O)C.C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]([CH3:15])[C:11]([OH:13])=[O:12])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]

Komponenten

7

Edukt 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 70855557Methyl 2-(3-chloro-4-cyanophenyl)propanoate

Produkt 1

HCID 708476592-(3-Chloro-4-cyanophenyl)propanoic acidAusbeute 110,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred solution of methyl 2-(3-chloro-4-cyanophenyl)propanoate (642 mg, 2.87 mmol) in co-solvent with tetrahydrofuran and water (1:1) were added sodium hydroxide (287 mg, 7.175 mmol). The reaction mixture was stirred for 15 h at room temperature, then acidified to pH 3-4 with acetic acid. The residue dissolved in ethyl acetate and washed with water and brine. The organic layer was dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography. 2-(3-Chloro-4-cyanophenyl)propanoic acid (665 mg) was obtained as 99% yield.

Aufarbeitung

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customThe filtrate removed in vacuo
  5. customThe crude was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-afdd5c59efa14ac0b076d4c29a0434ff
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08937092B2

Notizen zur Reaktion

Wird geladen…