Methanol → 2-(4-Methylphenyl)benzoic acid

HRID 847048Notes

Reaction equation

HRID 847048 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]([O:16]C)=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.[OH-].[K+].CO>O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]([OH:16])=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 1393873(1,1'-Biphenyl)-2-carboxylic acid, 4'-methyl-, methyl ester

Product 1

HCID 815682-(4-Methylphenyl)benzoic acidYield 92.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl 4'-methylbiphenyl-2-carboxylate (10.0 g, 44.2 mmol, 1 eq), 0.5N KOH in methanol (265.5 mL, 133 mmol, 3 eq), and water (50 mL) were mixed and refluxed under N2. After 5 hours, the solvent was removed in vacuo and water (200 mL) and ethyl acetate (200 mL) added. The aqueous layer was acidified with concentrated hydrochloric acid to a pH of 3 and the layers were separated. The aqueous phase was extracted with ethyl acetate (2×200 mL), the organic layers collected, dried (MgSO4) and the solvent removed in vacuo to yield 8.71 g of a white solid; m.p. 140.0°-145.0° . NMR (200 MHz, DMSO-d6) δ7.72 (d, 1H, J=7 Hz); 7.56 (t, 1H, J=7 Hz); 7.45 (d, 1H, J=7 Hz); 7.40 (t, 1H, J=7 Hz); 7.25 (s, 4H); 2.36 (s, 3H). Anal. Calcd. for C14H12O2 ; C, 79.23; H, 5.70. Found: C, 79.22; H, 5.47.

Workup

  1. temperaturerefluxed under N2
  2. customthe solvent was removed in vacuo and water (200 mL) and ethyl acetate (200 mL)
  3. additionadded
  4. customthe layers were separated
  5. extractionThe aqueous phase was extracted with ethyl acetate (2×200 mL)
  6. customthe organic layers collected
  7. dry with materialdried (MgSO4)
  8. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-4c03f4e019b8424a815f015d04490b66
Source dataset
uspto-grants-1992_08
Patent number
US05138069

Reaction notes

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