Sodium Hydroxide → 2-(3-methoxyphenyl)benzoic Acid

HRID 278166Notes

Reaction equation

HRID 278166 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:19]=[CH:18][CH:17]=[CH:16][C:10]=2[C:11]([O:13]CC)=[O:12])[CH:6]=[CH:7][CH:8]=1.[OH-].[Na+]>CO.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:19]=[CH:18][CH:17]=[CH:16][C:10]=2[C:11]([OH:13])=[O:12])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22627113Ethyl 3'-methoxy-[1,1'-biphenyl]-2-carboxylate

Product 1

HCID 27595492-(3-methoxyphenyl)benzoic Acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of ethyl 2-(3-methoxyphenyl)benzoate from Step A (7.33 g, 28.6 mmol) in MeOH (200 mL) and water (30 mL) was added 1.0 N aq. NaOH (63 mL, 63 mmol) dropwise. The mixture was heated to reflux for 3 hours, then allowed to cool overnight. The solution was concentrated to remove most of the MeOH, cooled on ice, and 10% aq. citric acid (300 mL) was added. The resulting mixture was extracted with CH2Cl2 (3×250 mL), and the combined organic extracts were dried over Na2SO4, filtered, and concentrated under reduced pressure to give the titled product as a white solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 hours
  3. temperatureto cool overnight
  4. concentrationThe solution was concentrated
  5. customto remove most of the MeOH
  6. temperaturecooled on ice, and 10% aq. citric acid (300 mL)
  7. additionwas added
  8. extractionThe resulting mixture was extracted with CH2Cl2 (3×250 mL)
  9. dry with materialthe combined organic extracts were dried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-760fa2200bc847c787062babb705f813
Source dataset
uspto-grants-2002_03
Patent number
US06358985B1

Reaction notes

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