Methanol → 2-(4-Methylphenyl)benzoic acid

HRID 1368962Notes

Reaction equation

HRID 1368962 reaction equation
C[C:2]1[CH:3]=[C:4]([C:14]([O:16]C)=[O:15])[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][CH:7]=1.[OH-].[K+].[CH3:20]O>O>[CH3:20][C:11]1[CH:10]=[CH:9][C:8]([C:5]2[C:4]([C:14]([OH:16])=[O:15])=[CH:3][CH:2]=[CH:7][CH:6]=2)=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 18518531HCID 18518531, compound

Product 1

HCID 815682-(4-Methylphenyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl 4-methylbiphenyl-2-carboxylate (10.0 g, 44.2 mmol, 1 eq), 0.5 N 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 ml 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 y3=to yield 8.71 g of a white solid; m.p. 140.0°-145.0° NMR (206 MHz, DMSO-d6 δ 7.72 (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 (9, 411); 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 ml 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 y3=to yield 8.71 g of a white solid

Sources & evidence

ORD record
ord-86053824359c46c097e2db38573f9abc
Source dataset
uspto-grants-2003_06
Patent number
US06576652B2

Reaction notes

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