Hydrochloric Acid → 4-{4,4-Dimethyl-1-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-pentyloxy}-benzoic acid

HRID 1669311Notes

Reaction equation

HRID 1669311 reaction equation
C[O:2][C:3](=[O:34])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH:11]([C:18]2[CH:19]=[N:20][C:21]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=3)=[CH:22][CH:23]=2)[CH2:12][CH2:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:6][CH:5]=1.[OH-].[Na+].Cl>C1COCC1>[CH3:15][C:14]([CH3:17])([CH3:16])[CH2:13][CH2:12][CH:11]([C:18]1[CH:19]=[N:20][C:21]([C:24]2[CH:25]=[CH:26][C:27]([C:30]([F:33])([F:31])[F:32])=[CH:28][CH:29]=2)=[CH:22][CH:23]=1)[O:10][C:7]1[CH:6]=[CH:5][C:4]([C:3]([OH:34])=[O:2])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 673421814-{4,4-Dimethyl-1-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-pentyloxy}-benzoic acid methyl ester

Product 1

HCID 673429454-{4,4-Dimethyl-1-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-pentyloxy}-benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-{4,4-Dimethyl-1-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-pentyloxy}-benzoic acid methyl ester (isomer 2) is taken into THF (1.0 mL) and treated with NaOH (1.0 mL, 5.0 N), then refluxed under nitrogen. The reaction mixture is neutralized with HCl (1.0 mL, 5.0 N), extracted with ethyl ether, dried over sodium sulfate. Concentration gives the title compound, (180 mg, 0.38 mmol), 55%.

Workup

  1. temperaturerefluxed under nitrogen
  2. extractionextracted with ethyl ether
  3. dry with materialdried over sodium sulfate
  4. concentrationConcentration

Sources & evidence

ORD record
ord-c546fb94783b434ab69cf866de34a1ff
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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