Water → m-tert-Butylbenzoic acid

HRID 1610745Notes

Reaction equation

HRID 1610745 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:17]=[CH:18][CH:19]=1)[CH2:8]C1C=CC=CC=1C#N)([CH3:4])([CH3:3])[CH3:2].[OH-:20].[Na+].[OH2:22]>>[C:1]([C:5]1[CH:6]=[C:7]([CH:17]=[CH:18][CH:19]=1)[C:8]([OH:22])=[O:20])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 962Water2×HCID 14798Sodium HydroxideHCID 22261964HCID 22261964, compound

Product 1

HCID 139037m-tert-Butylbenzoic acidYield 83%

Procedure

To a suspension of 3-tert-butylbenzylbenzonitrile (4.13 g, 21.9 mmol) in water (80 ml) was added sodium hydroxide (2.19 g, 54.8 mmol) and the mixture was heated under reflux overnight. After completion of the reaction, the mixture was diluted with water, and the aqueous layer was washed with ether. The aqueous layer was then acidified with 6N hydrochloric acid, and extracted with ethyl acetate. The combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to give 3-tert-butylbenzoic acid (3.23 g, 83% in 2 steps) as colorless crystals.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight
  3. customAfter completion of the reaction
  4. washthe aqueous layer was washed with ether
  5. extractionextracted with ethyl acetate
  6. washThe combined organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fd5eddb9dc7345bcb8620dad6a477b4e
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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