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

HRID 888623Notes

Reaction equation

HRID 888623 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-200eb55b7c2545a1bbae29dd293c364d
Source dataset
uspto-grants-2012_08
Patent number
US08247576B2

Reaction notes

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