Hydrochloric Acid → HCID 86588524, compound

HRID 1582799Notes

Reaction equation

HRID 1582799 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([CH2:31][CH2:32][CH2:33][C:34]([F:40])([F:39])[C:35]([F:38])([F:37])[F:36])([C:26]([O:28]CC)=[O:27])[C:21]([O:23]CC)=[O:22])=[C:8]([C:41]1[CH:46]=[CH:45][C:44]([O:47][CH3:48])=[CH:43][CH:42]=1)[CH:7]=[CH:6]2.[OH-].[Na+].O.Cl>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([CH2:31][CH2:32][CH2:33][C:34]([F:40])([F:39])[C:35]([F:38])([F:37])[F:36])([C:26]([OH:28])=[O:27])[C:21]([OH:23])=[O:22])=[C:8]([C:41]1[CH:46]=[CH:45][C:44]([O:47][CH3:48])=[CH:43][CH:42]=1)[CH:7]=[CH:6]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 20726890HCID 20726890, compound

Product 1

HCID 86588524HCID 86588524, compoundYield 106.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Diethyl 2-[7-[6-methoxy-2-(4-methoxyphenyl)napht-1-yl]heptyl]-2-(4,4,5,5,5-pentafluoropentyl)malonate (1.02 g, 1.5 mmol) was dissolved in ethanol (10 ml). To this solution, sodium hydroxide (1.2 g, 30 mmol) and water (1 ml) were added, and the resulting mixture was heated under reflux for 3 hours. Dilute hydrochloric acid was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled off to give 2-[7-[6-methoxy-2-(4-methoxyphenyl)napht-1-yl]heptyl]-2-(4,4,5,5,5-pentafluoropentyl)malonic acid (1.0 g).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 3 hours
  3. extractionwas then extracted with ethyl acetate
  4. washThe organic layer was washed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-ed40ce66302f438abf1eedd8f0ddbf93
Source dataset
uspto-grants-2004_05
Patent number
US06737417B2

Reaction notes

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