Sodium Hydroxide → 5-Methylbiphenyl-2-carboxylic acid

HRID 2121201Notes

Reaction equation

HRID 2121201 reaction equation
C[O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:5]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[OH-].[Na+]>CO>[CH3:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:17])=[O:2])=[C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 18474515HCID 18474515, compound

Product 1

HCID 154962685-Methylbiphenyl-2-carboxylic acidYield 97.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-methyl-2-phenylbenzoic acid methyl ester (1.83 g, 8.09 mmol), prepared as in Example 227A, in methanol (16 mL) was added aqueous 4N sodium hydroxide (5 mL) and the reaction mixture was stirred for 60 hours, after which additional aqueous 4N sodium hydroxide (5 mL) was added and the mixture was heated at reflux for 5 hours. The reaction mixture was cooled to ambient temperature and the methanol was evaporated in vacuo. The aqueous residue was acidified with 4N sulfuric acid and extracted with ethyl acetate (3×). The combined organic extracts were dried, filtered, and concentrated in vacuo to give 4-methyl-2-phenylbenzoic acid (1.67 g) as a white solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 5 hours
  3. customthe methanol was evaporated in vacuo
  4. extractionextracted with ethyl acetate (3×)
  5. customThe combined organic extracts were dried
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-09d8500c06cd409896b6f4fcfa991776
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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