Hydrochloric Acid → Ethyl 4-(2-oxo-1-cyclopentylidenemethyl)phenylacetate

HRID 127013Notes

Reaction equation

HRID 127013 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:5][CH:4]=1)=O.N1([C:20]2[CH2:24][CH2:23][CH2:22][CH:21]=2)CCCC1.Cl.[OH2:26]>C1C=CC=CC=1>[O:26]=[C:20]1[CH2:24][CH2:23][CH2:22][C:21]1=[CH:1][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 81570Pyrrolidine, 1-(1-cyclopenten-1-yl)-HCID 11310039Ethyl 2-(4-formylphenyl)acetate

Product 1

HCID 54231923Ethyl 4-(2-oxo-1-cyclopentylidenemethyl)phenylacetate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A mixture of 3.7 g of ethyl p-formylphenylacetate, 5.2 g of pyrrolidinocyclopentene and 20 ml of benzene was heated under reflux for 13 hours. After cooling, 5 ml of conc. hydrochloric acid and 5 ml of water were added to the reaction mixture and the resulting mixture was stirred at room temperature overnight. To the mixture added 100 ml of benzene, a benzene layer was separated, washed with water and dried over anhydrous sodium sulfate. Thereafter, the benzene was distilled off and the residue was subjected to a silica gel column chromatography. Elution was effected with benzene-ethyl acetate 50:1 to give an oily substance, which was then distilled under reduced pressure to afford 0.5 g of an oily substance having a boiling point of 175°-180° C./0.3 mmHg (bath temp.).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 13 hours
  3. temperatureAfter cooling
  4. customa benzene layer was separated
  5. washwashed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThereafter, the benzene was distilled off
  8. washElution
  9. customto give an oily substance, which
  10. distillationwas then distilled under reduced pressure
  11. customto afford 0.5 g of an oily substance

Sources & evidence

ORD record
ord-de9d194c852549b19370d968b4d54313
Source dataset
uspto-grants-1981_03
Patent number
US04254274

Reaction notes

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