Hydrochloric Acid → 2-(3,5-Bis(trifluoromethyl)phenyl)-2-methylpropanoic acid

HRID 1392974Notes

Reaction equation

HRID 1392974 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:4]=[C:5]([C:13]([CH3:19])([CH3:18])[C:14]([O:16]C)=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[OH-].[K+].Cl>CO>[F:1][C:2]([F:20])([F:21])[C:3]1[CH:4]=[C:5]([C:13]([CH3:18])([CH3:19])[C:14]([OH:16])=[O:15])[CH:6]=[C:7]([C:9]([F:11])([F:12])[F:10])[CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 219553242-(3,5-Bis-trifluoromethyl-phenyl)-2-methylpropionic acid, methyl ester

Product 1

HCID 98359482-(3,5-Bis(trifluoromethyl)phenyl)-2-methylpropanoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-(3,5-bis-trifluoromethyl-phenyl)-2-methyl-propionic acid, methyl ester (intermediate 69-184 mg) and potassium hydroxide (131 mg) in MeOH (2.5 mL) was heated to reflux for 1 hour, then it was allowed to cool to r.t. and acidified to pH=3 with 10% hydrochloric acid solution and extracted with AcOEt (2×10 mL). The combined organic extracts were dried and concentrated in vacuo to a residue which was purified by flash chromatography (CH/AcOEt from 8:2 to 6:4) to give the title compound (141 mg) as a white solid.

Workup

  1. temperatureto reflux for 1 hour
  2. extractionextracted with AcOEt (2×10 mL)
  3. customThe combined organic extracts were dried
  4. concentrationconcentrated in vacuo to a residue which
  5. customwas purified by flash chromatography (CH/AcOEt from 8:2 to 6:4)

Sources & evidence

ORD record
ord-5acf63bc1ca3413298bcd7a21f0e91f2
Source dataset
uspto-grants-2008_03
Patent number
US07345041B2

Reaction notes

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