Hydrochloric Acid → Ethyl 2-[4-(2-oxo-1-cyclopentylidenemethyl)phenyl]propionate

HRID 127009Notes

Reaction equation

HRID 127009 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:5][CH:4]=1)=O.O1CCN([C:22]2[CH2:26][CH2:25][CH2:24][CH:23]=2)CC1.Cl.[OH2:28]>C1C=CC=CC=1>[O:28]=[C:22]1[CH2:26][CH2:25][CH2:24][C:23]1=[CH:1][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 702941-MorpholinocyclopenteneHCID 13066570rac 2-(4-Formylphenyl)propionic Acid Ethyl Ester

Product 1

HCID 53946190Ethyl 2-[4-(2-oxo-1-cyclopentylidenemethyl)phenyl]propionate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A mixture of 5.15 g of ethyl 2-(p-formylphenyl)propionate and 4.5 g of morpholinocyclopentene in 10 ml of benzene was heated under reflux for 10 hours. After cooling, a mixture of 5 ml of conc. hydrochloric acid and 5 ml of water was added to the reaction mixture under ice-cooling and the resulting mixture was stirred at room temperature overnight. After addition of 100 ml of benzene, an organic layer was separated, washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off to leave an oily substance, which was then distilled under reduced pressure to give 5.3 g of the desired product having a boiling point of 160°-165° C./0.25 mmHg.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 10 hours
  3. temperatureAfter cooling
  4. additionwas added to the reaction mixture under ice-
  5. temperaturecooling
  6. customan organic layer was separated
  7. washwashed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationThe solvent was distilled off
  10. customto leave an oily substance, which
  11. distillationwas then distilled under reduced pressure

Sources & evidence

ORD record
ord-a09fc7a81109467da49f1cc8e6bd82e8
Source dataset
uspto-grants-1981_03
Patent number
US04254274

Reaction notes

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