2,2-Bis-(4-chloro-phenyl)-propionic acid methyl ester → 2,2-Bis(4-chlorophenyl)propanoic acid

HRID 45554Notes

Reaction equation

HRID 45554 reaction equation
C[O:2][C:3](=[O:20])[C:4]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)([C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1)[CH3:5]>C1COCC1.O.CO>[Cl:12][C:9]1[CH:8]=[CH:7][C:6]([C:4]([C:13]2[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=2)([CH3:5])[C:3]([OH:20])=[O:2])=[CH:11][CH:10]=1

Participants

3

Reactant 1

HCID 235629742,2-Bis-(4-chloro-phenyl)-propionic acid methyl ester

Product 1

HCID 135116882,2-Bis(4-chlorophenyl)propanoic acidYield 94.1%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A solution of 2,2-bis-(4-chloro-phenyl)-propionic acid methyl ester (210 mg, 0.67 mmol) in THF/water/methanol (1:1:1, 18 mL) was stirred at room temperature for 5 days then concentrated in vacuo. The residue was partitioned between ethyl acetate and 2N hydrochloric acid, then the organic phase was washed with brine, dried (MgSO4), filtered and concentrated to give the title compound (186 mg, 93%) as a yellow solid which was used without further purification. LCMS (PS-B3) Rt 2.40 min [M-CO2H]− 249.

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe residue was partitioned between ethyl acetate and 2N hydrochloric acid
  3. washthe organic phase was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-dff8c34977a445b5b1b879ec37e034e8
Source dataset
uspto-grants-2013_09
Patent number
US08541461B2

Reaction notes

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