Hydrochloric Acid → Hydroxy[bis(4-methylphenyl)]acetic acid

HRID 650525Notes

Reaction equation

HRID 650525 reaction equation
C[O:2][C:3](=[O:20])[C:4]([C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)([C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1)[OH:5].[OH-].[Na+].Cl>CO>[C:9]1([CH3:12])[CH:8]=[CH:7][C:6]([C:4]([C:13]2[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][CH:18]=2)([OH:5])[C:3]([OH:20])=[O:2])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22574226Di-p-tolylhydroxyacetic acid methyl ester

Product 1

HCID 229097Hydroxy[bis(4-methylphenyl)]acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 22 (613 mg, 2.26 mmol) in methanol (75 mL) was treated with 1 N NaOH (10 mL) at room temperature. The mixture was stirred at room temperature overnight. The mixture was neutralized with 1 N HCl and the solvent was removed in vacuo. The residue was dissolved in dichloromethane and 1 N HCl solution. The aqueous layer was extracted with two additional portions of dichloromethane and the combined organic extracts were washed with brine, dried over Na2SO4, and concentrated under reduced pressure to afford the title compound (23). The crude product was used directly.

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in dichloromethane
  3. extractionThe aqueous layer was extracted with two additional portions of dichloromethane
  4. washthe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c9934354e9db41dabc53da71157381a1
Source dataset
uspto-grants-2001_08
Patent number
US06274583B1

Reaction notes

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