Hydrochloric Acid → HCID 15062348, compound

HRID 1464195Notes

Reaction equation

HRID 1464195 reaction equation
[F:1][C:2]([F:32])([C:19]1[CH:24]=[CH:23][C:22]([CH:25]([CH3:31])[C:26]([O:28]CC)=[O:27])=[CH:21][CH:20]=1)[C:3]([F:18])([F:17])[C:4]([F:16])([F:15])[C:5]([F:14])([F:13])[C:6]([F:12])([F:11])[C:7]([F:10])([F:9])[F:8].Cl>C(O)C.[OH-].[Na+]>[F:1][C:2]([F:32])([C:19]1[CH:20]=[CH:21][C:22]([CH:25]([CH3:31])[C:26]([OH:28])=[O:27])=[CH:23][CH:24]=1)[C:3]([F:17])([F:18])[C:4]([F:15])([F:16])[C:5]([F:13])([F:14])[C:6]([F:12])([F:11])[C:7]([F:10])([F:9])[F:8]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 15062346HCID 15062346, compound

Product 1

HCID 15062348HCID 15062348, compoundYield 57.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

Ethyl 2-(4-[perfluorohexyl]phenyl)propionate (100 mg, 0.20 mmol) was dissolved in 5 mL of ethanol and 5 mL of 1N NaOH. The solution was heated to reflux for 1 hour, cooled to room temperature, poured into 30 mL of 1N HCl and extracted with three 10-mL portions of dicholormethane. Combination, drying (MgSO4), and concentration of the organic layers gave a residue which was purified by PTLC (one 2 mm silica gel plate eluted with 15% methanol-85% dichloromethane) to give 54 mg (57% yield) of 2-(4-[perflurohexyl]phenyl)propionic acid as a white powder.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 1 hour
  3. extractionextracted with three 10-mL portions of dicholormethane
  4. dry with materialCombination, drying (MgSO4), and concentration of the organic layers
  5. customgave a residue which
  6. customwas purified by PTLC (one 2 mm silica gel plate eluted with 15% methanol-85% dichloromethane)

Sources & evidence

ORD record
ord-0921cfaf73894568807986bbd7a86aa9
Source dataset
uspto-grants-1994_04
Patent number
US05302752

Reaction notes

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