Tetrahydrofuran → 2,6-Dimethoxybiphenyl-4-carboxylic acid

HRID 1096977Notes

Reaction equation

HRID 1096977 reaction equation
[OH-].[Na+].C1COCC1.[CH3:8][O:9][C:10]1[CH:15]=[C:14]([C:16]([O:18]C)=[O:17])[CH:13]=[C:12]([O:20][CH3:21])[C:11]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.OS([O-])(=O)=O.[K+]>CO>[CH3:21][O:20][C:12]1[CH:13]=[C:14]([C:16]([OH:18])=[O:17])[CH:15]=[C:10]([O:9][CH3:8])[C:11]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 516920Potassium bisulfateHCID 57930909Methyl 2,6-dimethoxybiphenyl-4-carboxylate

Product 1

HCID 167685332,6-Dimethoxybiphenyl-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

Aqueous 5 N sodium hydroxide solution (44 mL) was added to a THF (150 mL)-MeOH (150 mL) solution of methyl 2,6-dimethoxybiphenyl-4-carboxylate (20.0 g), and stirred at 40° C. for 5 hours. The reaction solution was poured into aqueous 0.5 M KHSO4 solution, and extracted with ethyl acetate. The combined organic layers were washed with aqueous saturated sodium chloride solution, dried with anhydrous sodium sulfate, and concentrated. The residue was recrystallized from hexane/ethyl acetate to obtain the title compound as a colorless crystal.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were washed with aqueous saturated sodium chloride solution
  3. dry with materialdried with anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was recrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-4a82116580c84db8b74ed2fb28c31eef
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

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