Hydrochloric Acid → 4-Biphenyl-(4'-methoxy)acetic acid

HRID 973516Notes

Reaction equation

HRID 973516 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16]([O:18]CC)=[O:17])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[OH-].[Na+].Cl>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16]([OH:18])=[O:17])=[CH:11][CH:10]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15733994Ethyl 4-(4-methoxyphenyl)phenylacetate

Product 1

HCID 13937004-Biphenyl-(4'-methoxy)acetic acidYield 232.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 250 mg (0.93 mmol) of ethyl 4-(4-methoxyphenyl)phenylacetate in 30 ml of ethanol was added, with cooling with ice, 5 ml of 40% sodium hydroxide aqueous solution. This mixture was stirred at room temperature for 2 days. The reaction mixture was neutralized with 3 M hydrochloric acid, and the solvent was then removed by evaporation under reduced pressure. Thereafter, the pH of the resulting mixture was adjusted to 1 with 3 M hydrochloric acid, and this mixture was subjected to extraction with 200 ml of ether. The resulting ether solution was washed with saturated sodium chloride aqueous solution, dried with anhydrous magnesium sulfate, filtered, and then concentrated. Thus, 524 mg (yield 94%) of 4-(4-methoxyphenyl)-phenylacetic acid was obtained.

Workup

  1. customthe solvent was then removed by evaporation under reduced pressure
  2. extractionthis mixture was subjected to extraction with 200 ml of ether
  3. washThe resulting ether solution was washed with saturated sodium chloride aqueous solution
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ffc56470144d42a0a83bac486b934897
Source dataset
uspto-grants-1991_11
Patent number
US05064564

Reaction notes

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