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

HRID 896519Notes

Reaction equation

HRID 896519 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-dimethyl-propionic acid ethyl ester (10.0 g, 44.6 mmol) and a solution of sodium hydroxide (25 g) in water (110 mL) was heated to reflux for 18 hours. The resulting solution was cooled to room temperature, then was stirred on ice and acidified to about pH 1 with concentrated aqueous hydrochloric acid. The resulting precipitate was collected by filtration, washed thoroughly with water, and dried under vacuum. The solid was stirred in dichloromethane, and the mixture was filtered to remove a residual gelatinous solid. The filtrate was concentrated to provide a pale yellowish solid (7.60 g, 87%) which was used without further purification. 1H NMR (300 MHz, CDCl3) δ7.14 (m, 2H), 6.98 (t, J=8 Hz, 2H), 2.88 (s, 2H), 1.22 (s, 6H). Mass spec (ES−) m/z 195.2 (M−H−, 100%).

Workup

  1. temperatureto reflux for 18 hours
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed thoroughly with water
  4. customdried under vacuum
  5. stirringThe solid was stirred in dichloromethane
  6. filtrationthe mixture was filtered
  7. customto remove a residual gelatinous solid
  8. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-2fe0392df4664d8baabd2319c9f435b3
Source dataset
uspto-grants-2005_07
Patent number
US06919356B2

Reaction notes

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