Hydrochloric Acid → 3-(4-Fluorophenyl)-2,2-dimethylpropanoic acid

HRID 1592331Notes

Reaction equation

HRID 1592331 reaction equation
C([O:3][C:4](=[O:16])[C:5]([CH3:15])([CH3:14])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1)C.[OH-].[Na+].Cl>O>[F:13][C:10]1[CH:9]=[CH:8][C:7]([CH2:6][C:5]([CH3:15])([CH3:14])[C:4]([OH:16])=[O:3])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69423048Ethyl 3-(4-fluorophenyl)-2,2-dimethylpropanoate

Product 1

HCID 223502093-(4-Fluorophenyl)-2,2-dimethylpropanoic acidYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-(4-fluorophenyl)-2,2-dimethylpropionic acid ethyl ester (10.0 g, 44.6 mmol, see Part 1 of Example 25a) and a solution of sodium hydroxide (25 g) in water (110 mL) was heated at reflux for 18 h and cooled to room temperature. The solution was stirred on an ice bath and acidified with concentrated aqueous hydrochloric acid. The resulting precipitate was collected by filtration, washed with water and dried under vacuum. The residue was stirred with dichloromethane and filtered, and the filtrate was concentrated to provide an off-white solid (7.60 g, 87%).

Workup

  1. temperatureat reflux for 18 h
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with water
  4. customdried under vacuum
  5. stirringThe residue was stirred with dichloromethane
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-cf126b75a27f4fce8171e2e2b442e4b3
Source dataset
uspto-grants-2007_11
Patent number
US07291744B2

Reaction notes

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