Methanol → 3-Methoxy-4-(2-methylphenyl)benzoic acid

HRID 639235Notes

Reaction equation

HRID 639235 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])=[C:7]([O:18][CH3:19])[CH:6]=1)=[O:4].CO.[OH-].[Na+]>O1CCCC1>[CH3:19][O:18][C:7]1[CH:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:10]=[CH:9][C:8]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:17]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 53941402Methyl 2-methoxy-2'-methylbiphenyl-4-carboxylate

Product 1

HCID 180010763-Methoxy-4-(2-methylphenyl)benzoic acidYield 87.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
105 °C

Procedure

To the 2-methoxy-2′-methyl-biphenyl-4-carboxylic acid methyl ester of step C (26 mmol) was added methanol (10 mL), tetrahydrofuran (45 mL) and 1 N sodium hydroxide (33 mL). The solution was refluxed vigorously in an oil bath at 105° C. for one hour. The volatile solvents were evaporated and the solution was chilled in ice. 2N hydrochloric acid was added until the pH was ˜1. The product was extracted into ethyl acetate, dried with anhydrous magnesium sulfate, and evaporated to a white solid. This was recrystallized from ethyl acetate/hexane to afford 5.5 g of title compound (86%).

Workup

  1. customThe volatile solvents were evaporated
  2. temperaturethe solution was chilled in ice
  3. addition2N hydrochloric acid was added until the pH was ˜1
  4. extractionThe product was extracted into ethyl acetate
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customevaporated to a white solid
  7. customThis was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-7f10b811aa024744bf8ca76282d17f55
Source dataset
uspto-grants-2010_04
Patent number
US07691848B2

Reaction notes

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