Hydrochloric Acid → Ethyl2-[4-(2-oxo-1-cyclohexylidenemethyl)phenyl]propionate

HRID 127008Notes

Reaction equation

HRID 127008 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.N1([C:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH:22]=2)CCCC1.Cl.[OH2:28]>C1C=CC=CC=1>[CH2:13]([O:12][C:10](=[O:11])[CH:9]([C:6]1[CH:7]=[CH:8][C:3]([CH:1]=[C:22]2[CH2:23][CH2:24][CH2:25][CH2:26][C:21]2=[O:28])=[CH:4][CH:5]=1)[CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 707681-Pyrrolidino-1-cyclohexeneHCID 13066570rac 2-(4-Formylphenyl)propionic Acid Ethyl Ester

Product 1

HCID 54259840Ethyl2-[4-(2-oxo-1-cyclohexylidenemethyl)phenyl]propionate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A mixture of 5.15 g of ethyl 2-(p-formylphenyl)propionate, 4.5 g of pyrrolidinocyclohexene and 20 ml of benzene was heated under reflux for 18 hours. After cooling, the reaction mixture was admixed with a mixture of 5 ml of conc. hydrochloric acid and 5 ml of water under ice-cooling and then stirred at room temperature overnight. 100 ml of benzene were added thereto, the organic layer was separated and then washed with water. After drying over anhydrous sodium sulfate, the benzene was distilled off to leave an oily substance. The substance was distilled under reduced pressure to afford 2.3 g of the desired product as a yellow oily substance having a boiling point of 160°-170° C./0.3 mmHg (bath temp.).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 hours
  3. temperatureAfter cooling
  4. temperaturecooling
  5. customthe organic layer was separated
  6. washwashed with water
  7. dry with materialAfter drying over anhydrous sodium sulfate
  8. distillationthe benzene was distilled off
  9. customto leave an oily substance
  10. distillationThe substance was distilled under reduced pressure

Sources & evidence

ORD record
ord-5218d274ac734aa8a9187f0fa2d65feb
Source dataset
uspto-grants-1981_03
Patent number
US04254274

Reaction notes

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