Hydrochloric Acid → HCID 10835551, compound

HRID 1728997Notes

Reaction equation

HRID 1728997 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[C:7]([O:10][CH3:11])[C:6]([O:12][CH3:13])=[C:5]([CH3:14])[C:4]=1/[CH:15]=[C:16](\[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1)/[C:17]([O:19]CC)=[O:18].[OH-].[Na+].Cl>C(O)C>[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[C:7]([O:10][CH3:11])[C:6]([O:12][CH3:13])=[C:5]([CH3:14])[C:4]=1/[CH:15]=[C:16](\[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1)/[C:17]([OH:19])=[O:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10623034HCID 10623034, compound

Product 1

HCID 10835551HCID 10835551, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

177 g (0.39 mol) of the ester prepared in Example 1 was dissolved in 500 ml of ethanol, followed by the addition of 100 ml of an aqueous solution of 78 g of sodium hydroxide. The obtained mixture was heated under reflux for one hour, followed by the addition of 1 l of ice. The obtained mixture was neutralized with 6N hydrochloric acid. The resulting mixture was extracted with 1 l of ethyl acetate twice. The organic layer was washed with an aqueous solution of sodium chloride, dried over magnesium sulfate and distilled to remove the solvent. 159 g of the title compound was obtained as a colorless oil.

Workup

  1. temperatureThe obtained mixture was heated
  2. temperatureunder reflux for one hour
  3. extractionThe resulting mixture was extracted with 1 l of ethyl acetate twice
  4. washThe organic layer was washed with an aqueous solution of sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. distillationdistilled
  7. customto remove the solvent

Sources & evidence

ORD record
ord-788361b7c98848acab2363d0fb160a6a
Source dataset
uspto-grants-1994_07
Patent number
US05329010

Reaction notes

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