4-Methyl-alpha-(4-methylphenyl)benzeneacetic acid → Benzeneacetic acid, 4-methyl-alpha-(4-methylphenyl)-, methyl ester

HRID 650523Notes

Reaction equation

HRID 650523 reaction equation
[C:1]1([CH3:18])[CH:6]=[CH:5][C:4]([CH:7]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)[C:8]([OH:10])=[O:9])=[CH:3][CH:2]=1.Cl.[CH3:20]O>CO>[C:14]1([CH3:17])[CH:13]=[CH:12][C:11]([CH:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:18])=[CH:2][CH:3]=2)[C:8]([O:10][CH3:20])=[O:9])=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 303144-Methyl-alpha-(4-methylphenyl)benzeneacetic acidHCID 21893726Hydrochloride methanol

Product 1

HCID 6452857Benzeneacetic acid, 4-methyl-alpha-(4-methylphenyl)-, methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of di-p-tolylacetic acid (4.90 g, 20.4 mmol) in methanol was treated with sat'd HCl/MeOH solution at room temperature. The mixture was stirred at room temperature (3 h). The solvent was removed in vacuo and the residue dissolved in dichloromethane and sodium bicarbonate 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 (21). The crude product was used directly.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue 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-457f78703e844a13b2f9a4ea3ef6e8db
Source dataset
uspto-grants-2001_08
Patent number
US06274583B1

Reaction notes

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