Hydrochloric Acid → HCID 21088683, compound

HRID 350739Notes

Reaction equation

HRID 350739 reaction equation
[C:1]1([C:7]2[N:8]=[C:9](/[CH:16]=[CH:17]/[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[O:10][C:11]=2[CH2:12][CH2:13][C:14]#N)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-:24].[Na+].[OH2:26].Cl>C(O)C>[C:1]1([C:7]2[N:8]=[C:9](/[CH:16]=[CH:17]/[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[O:10][C:11]=2[CH2:12][CH2:13][C:14]([OH:26])=[O:24])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 21088684HCID 21088684, compound

Product 1

HCID 21088683HCID 21088683, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-[4-phenyl-2-((E)-2-phenylethenyl)-5-oxazolyl]propionitrile (1.3 g) in ethanol (18 mL) was added 2N aqueous sodium hydroxide solution (9 mL) and the mixture was stirred with heating under reflux for 5 hrs. The reaction mixture was cooled and water was added. The mixture was acidified with 2N aqueous hydrochloric acid solution, and extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The precipitated crystals were collected by filtration and recrystallized from ethanol to give 3-[4-phenyl-2-((E)-2-phenylethenyl)-5-oxazolyl]propionic acid (0.9 g, yield 65%) as colorless prism crystals. melting point: 138–139° C.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 5 hrs
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed successively with water and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. filtrationThe precipitated crystals were collected by filtration
  9. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-a4f5f64a00284a309c403639e1a6dee9
Source dataset
uspto-grants-2007_02
Patent number
US07183276B2

Reaction notes

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