Methyl 6-methoxy-[1,1'-biphenyl]-3-carboxylate → 4-Methoxy-3-phenylbenzoic acid

HRID 423327Notes

Reaction equation

HRID 423327 reaction equation
[CH3:1][O:2][C:3]1[C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:7][C:6]([C:15]([O:17]C)=[O:16])=[CH:5][CH:4]=1>[OH-].[Na+].CO>[CH3:1][O:2][C:3]1[C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:7][C:6]([C:15]([OH:17])=[O:16])=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 11010121Methyl 6-methoxy-[1,1'-biphenyl]-3-carboxylate

Product 1

HCID 167688254-Methoxy-3-phenylbenzoic acidYield 110.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

Methyl 6-(methyloxy)-3-biphenylcarboxylate (D39) (194 mg, 0.8 mmol) dissolved in 2N NaOH aq. (3 ml) and methanol (3 ml). Stirred at room temperature overnight and then the organic solvent was evaporated in vacuo. Added EtOAc/water separated and then acidified the aqueous and re-extracted. The organic extracts were dried and evaporated to afford 202 mg of the title compound as a white solid. δH (d6-DMSO, 400 MHz) 3.84 (3H, s), 7.22 (1H, d), 7.33-7.49 (5H, m), 7.82 (1H, d), 7.95 (1H, dd), MS (ES+): C14H12O3 requires 228; found 229 (M+H+).

Workup

  1. customthe organic solvent was evaporated in vacuo
  2. customAdded EtOAc/water separated
  3. extractionre-extracted
  4. customThe organic extracts were dried
  5. customevaporated

Sources & evidence

ORD record
ord-b2369f6f04824e2e81a2d47544c22467
Source dataset
uspto-grants-2012_01
Patent number
US08101775B2

Reaction notes

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