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

HRID 1419456Notes

Reaction equation

HRID 1419456 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Conditions

Temperature
5 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-b6c27a107e314b1abbef34fc6a53467b
Source dataset
uspto-grants-1999_03
Patent number
US05886156

Reaction notes

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