Sodium Methoxide → o-Phenylbenzoic acid

HRID 650323Notes

Reaction equation

HRID 650323 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:6][CH:7]=1.Cl[C:20]1[CH2:25][CH2:24][C:23]([C:26]([O:28]CC)=[O:27])=[C:22]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:21]=1.C[O-].[Na+]>CO>[C:13]1([C:4]2[CH:3]=[CH:2][CH:7]=[CH:6][C:5]=2[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1.[C:31]1([C:22]2[CH:21]=[CH:20][CH:25]=[CH:24][C:23]=2[C:26]([OH:28])=[O:27])[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

6

Reactant 3

HCID 10942334Sodium MethoxideHCID 10967324HCID 10967324, compoundHCID 11043594HCID 11043594, compound

Product 2

HCID 70357o-Phenylbenzoic acidYield 53.8%HCID 9920952Ethyl 2-phenylbenzoateYield 23.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of a mixture(620 mg, 2.54 mmol) of ethyl 4-chloro-2-phenylcyclohexa-2,4-dienecarboxylate and ethyl 4-chloro-2-phenylcyclohexa-1,3-dienecarboxylate in MeOH(5 ml), NaOMe(28% in MeOH, 1.98 g, 10.1 mmol) was added. After stirring for 17 hr at room temperature, the solvent was evaporated under reduced pressure. Water was added to the residue and dil. HCl aq., and it was extracted with AcOEt. The organic layer was washed with brine and dried over MgSO4. After removal of the solvent, the residue was purified by column chromatography on silica gel with n-hexane-AcOEt to afford 136 mg of ethyl 2-phenylbenzoate(y=23.7%) and 236 mg of 2-phenylbenzoic acid(y=53.8%). 1H-NMR(ppm, 300 MHz, CDCl3) δ ester 7.82(1H, dd, J=1.4 and 7.7 Hz), 7.10-7.60(8H), 4.08(2H, d, J=7.0 Hz), 0.98(3H, t, J=7.0 Hz); acid 7.95(1H, d, J=7.9 Hz)

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. additionWater was added to the residue and dil. HCl aq., and it
  3. extractionwas extracted with AcOEt
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. customAfter removal of the solvent
  7. customthe residue was purified by column chromatography on silica gel with n-hexane-AcOEt

Sources & evidence

ORD record
ord-f9f8569fcc134b5380064cebe3fa2c8c
Source dataset
uspto-grants-2001_08
Patent number
US06271418B1

Reaction notes

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