Lithium Hydroxide → 2-Chloro-4-methylbenzoic acid

HRID 351121

Reaktionsgleichung

Reaktionsgleichung von HRID 351121
[Cl:1][C:2]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].[Li+].[OH-]>C1COCC1.O>[Cl:1][C:2]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Komponenten

5

Edukt 2

HCID 3939Lithium HydroxideHCID 22019481Methyl 2-chloro-4-methylbenzoate

Produkt 1

HCID 27357552-Chloro-4-methylbenzoic acidAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To methyl 2-chloro-4-methylbenzoate (1.00 g, 5.42 mmol) in THF (10 mL) MeOH (5 mL) and H2O (2.5 mL) is added 2N LiOH (8.12 mL, 16.2 mmol). The reaction mixture is heated at 50° C. for 2.5 hr, cooled to room temperature, then quenched with 5N HCl (3.24 mL). The mixture is concentrated to remove the TBF and MeOH. A white precipitate is formed and is filtered. After drying, 0.922 g (100%) of 2-chloro-4-methylbenzoic acid is isolated. ESIMS m/e 169 (M−−1; 35Cl) and 171 (M−−1; 37Cl).

Aufarbeitung

  1. temperaturecooled to room temperature
  2. customquenched with 5N HCl (3.24 mL)
  3. concentrationThe mixture is concentrated
  4. customto remove the TBF and MeOH
  5. customA white precipitate is formed
  6. filtrationis filtered
  7. customAfter drying

Quellen und Nachweise

ORD-Eintrag
ord-16269d7e8d644fbea34327e0fb2c6251
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07183320B2

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