Potassium Hydroxide → 3-(2',4'-Difluoro-biphenyl-4-yloxymethyl)-benzoic acid

HRID 1665234Notes

Reaction equation

HRID 1665234 reaction equation
C[O:2][C:3](=[O:26])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=3[F:25])=[CH:14][CH:13]=2)[CH:5]=1.[OH-].[K+]>CO>[F:25][C:19]1[CH:20]=[C:21]([F:24])[CH:22]=[CH:23][C:18]=1[C:15]1[CH:14]=[CH:13][C:12]([O:11][CH2:10][C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=2)[C:3]([OH:26])=[O:2])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 671503633-(2',4'-Difluoro-biphenyl-4-yloxymethyl)-benzoic acid methyl ester

Product 1

HCID 582711993-(2',4'-Difluoro-biphenyl-4-yloxymethyl)-benzoic acidYield 99.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-(2′,4′-Difluoro-biphenyl-4-yloxymethyl)-benzoic acid methyl ester (4.2 g, 11.86 mmol) and 2N KOH (23.72 mL, 47.45 mmol) in 210 mL MeOH were refluxed for 1 hr. The reaction mixture was cooled, concentrated and distributed into 200 mL H2O and 200 mL ethyl acetate. The aqueous layer was acidified with 2N HCl and separated. The organic layer was washed with saturated NaCl, dried over MgSO4, filtered and concentrated in vacuo to yield 4.0 g (99.1%) of 3-(2′,4′-difluoro-biphenyl-4-yloxymethyl)-benzoic acid as a white powder. LC-MS (ES) calculated for C20H14F2O3, 340.33; found m/z 339.1 [M−H]−.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated
  3. customseparated
  4. washThe organic layer was washed with saturated NaCl
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9107387444b64c24ad821fc15f64017a
Source dataset
uspto-grants-2011_10
Patent number
US08039495B2

Reaction notes

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