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

HRID 924763Notes

Reaction equation

HRID 924763 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-d41be0f840eb46a1a9c64481bf3584d9
Source dataset
uspto-grants-2016_03
Patent number
US09283226B2

Reaction notes

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