Carbon Dioxide → 5-(tert-Butyl)-4-hydroxy-m-toluic acid

HRID 1419456

Reaktionsgleichung

Reaktionsgleichung von HRID 1419456
[H-].[Na+].[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[C:8]=1[OH:14])([CH3:6])([CH3:5])[CH3:4].[C:15](=[O:17])=[O:16]>COCCOC>[C:3]([C:7]1[CH:12]=[C:11]([CH:10]=[C:9]([CH3:13])[C:8]=1[OH:14])[C:15]([OH:17])=[O:16])([CH3:6])([CH3:5])[CH3:4]

Komponenten

5

Edukt 3

HCID 280Carbon DioxideHCID 166782-tert-Butyl-6-methylphenolHCID 24758Sodium hydride

Produkt 1

HCID 44018175-(tert-Butyl)-4-hydroxy-m-toluic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

Charge a reaction vessel with a suspension of sodium hydride (4.74 g, 0.198 mol) in anhydrous ethylene glycol dimethyl ether (150 mL). Add, by dropwise addition, a solution of 2-t-butyl-6-methylphenol (0.1 mol) in ethylene glycol dimethyl ether (150 mL). Warm to 50°-60° C. for 1.5 hours then introduce carbon dioxide through a gas-disparging tube below the surface of the reaction mixture for 20 hours. Cool to 5° C. and destroy the excess sodium hydride carefully with methyl alcohol (30 mL). After hydrogen evolution ceases, adjust the pH of the reaction mixture to 2 with 1N hydrochloric acid. Dilute with water (1.6 L) and collect the title compound by filtration.

Aufarbeitung

  1. additionCharge a reaction vessel
  2. additionAdd, by dropwise addition
  3. temperatureWarm to 50°-60° C. for 1.5 hours
  4. customdestroy the excess sodium hydride carefully with methyl alcohol (30 mL)
  5. additionDilute with water (1.6 L)
  6. customcollect the title compound
  7. filtrationby filtration

Quellen und Nachweise

ORD-Eintrag
ord-b6c27a107e314b1abbef34fc6a53467b
Quelldatensatz
uspto-grants-1999_03
Patentnummer
US05886156

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