Hydrochloric Acid → (2'-Formyl-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid

HRID 1810239Notes

Reaction equation

HRID 1810239 reaction equation
C[O:2][C:3](=[O:25])[CH2:4][C:5]1[CH:6]=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:14]=2[CH:23]=[O:24])[C:8]([O:11][CH3:12])=[CH:9][CH:10]=1.[OH-].[Na+].Cl>CO.C1COCC1>[CH:23]([C:14]1[CH:15]=[C:16]([C:19]([F:22])([F:21])[F:20])[CH:17]=[CH:18][C:13]=1[C:7]1[C:8]([O:11][CH3:12])=[CH:9][CH:10]=[C:5]([CH2:4][C:3]([OH:25])=[O:2])[CH:6]=1)=[O:24]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86633167(2'-Formyl-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid methyl ester

Product 1

HCID 86651102(2'-Formyl-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To (2′-formyl-6-methoxy-4′-trifluoromethyl-biphenyl-3-yl)-acetic acid methyl ester (0.301 g, 0.85 mmol) in MeOH (2.4 mL) and THF (3 mL) was added aqueous 1N NaOH (1.9 mL), and the solution was stirred overnight at room temperature. Once no starting material was seen by analytical LCMS, the reaction was neutralized with aqueous 1N HCl and extracted with CH2Cl2. The combined organic layers were dried over MgSO4, filtered, and concentrated, and the residue was purified by silica gel chromatography (50-100% EtOAc in hexanes, followed by 5% MeOH in CH2Cl2) to give the title compound.

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthe residue was purified by silica gel chromatography (50-100% EtOAc in hexanes, followed by 5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-fb7c2acd4fec405d8c97075016c55172
Source dataset
uspto-grants-2013_01
Patent number
US08362044B2

Reaction notes

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