Methanol → 2-(4-Methylphenyl)benzoic acid

HRID 1737919Notes

Reaction equation

HRID 1737919 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), 0.5 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 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) 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 (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-1713d16114364a62aa8551f7688f3047
Source dataset
uspto-grants-1999_10
Patent number
US05962500

Reaction notes

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