Hydrochloric Acid → HCID 15062349, compound

HRID 1464196Notes

Reaction equation

HRID 1464196 reaction equation
[F:1][C:2]([F:38])([C:25]1[CH:30]=[CH:29][C:28]([CH:31]([CH3:37])[C:32]([O:34]CC)=[O:33])=[CH:27][CH:26]=1)[C:3]([F:24])([F:23])[C:4]([F:22])([F:21])[C:5]([F:20])([F:19])[C:6]([F:18])([F:17])[C:7]([F:16])([F:15])[C:8]([F:14])([F:13])[C:9]([F:12])([F:11])[F:10].Cl>C(O)C.[OH-].[Na+]>[F:1][C:2]([F:38])([C:25]1[CH:26]=[CH:27][C:28]([CH:31]([CH3:37])[C:32]([OH:34])=[O:33])=[CH:29][CH:30]=1)[C:3]([F:23])([F:24])[C:4]([F:21])([F:22])[C:5]([F:19])([F:20])[C:6]([F:17])([F:18])[C:7]([F:16])([F:15])[C:8]([F:14])([F:13])[C:9]([F:12])([F:11])[F:10]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 15062347HCID 15062347, compound

Product 1

HCID 15062349HCID 15062349, compoundYield 97.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

Ethyl 2-(4-[perfluorooctyl]phenyl)propionate (68 mg, 0.11 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 dichloromethane. Combination, drying (MgSO4), and concentration of the organic layers gave a residue which wa purified by PTLC (one 2 mm silica gel plate eluted with 15% methanol-85% dichloromethane) to give 61 mg (94% yield) of 2-(4-[perfluorooctyl]phenyl)propionic acid as a brown oil. The oil was recrystallized from dichloromethane to give brown crystals.

Workup

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

Sources & evidence

ORD record
ord-81a17fd35e764f2abd3509d51a0934f6
Source dataset
uspto-grants-1994_04
Patent number
US05302752

Reaction notes

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