Hydrochloric Acid → 4-Hydroxy-o-toluic acid

HRID 583809

Reaktionsgleichung

Reaktionsgleichung von HRID 583809
[CH3:1][C:2]1[CH:11]=[C:10]([O:12][Si](C)(C)C)[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].[Li+].[OH-].Cl>CO.O>[CH3:1][C:2]1[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 21879730Methyl 2-methyl-4-trimethylsilyloxybenzoate

Produkt 1

HCID 684754-Hydroxy-o-toluic acidAusbeute 31,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A 100 mL round bottom flask equipped with magnetic stir bar was charged with 5.7 g methyl 2-methyl-4-trimethylsilyloxybenzoate and 2.0 g LiOH in 40 mL methanol and 10 mL water. After 2 hours at reflux the reaction was poured into 10 mL concentrated HCl and then 100 g ice. Extraction with ethyl acetate followed by concentration in vacuo gave a crude solid (70:30) product:starting material. Flash Chromatography using 50—50 ethyl acetate/hexanes as an eluent gave 1.15 g 2-methyl-4-hydroxybenzoic acid, m/e=193 (M+H).

Aufarbeitung

  1. customA 100 mL round bottom flask equipped with magnetic stir bar
  2. temperatureAfter 2 hours at reflux the reaction
  3. extractionExtraction with ethyl acetate
  4. concentrationfollowed by concentration in vacuo
  5. customgave a crude solid (70:30) product

Quellen und Nachweise

ORD-Eintrag
ord-ba945a1148974ebd8c2017998c917847
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06924286B1

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