Benzaldehyde → 2-Phenylmethylenecyclopentanone

HRID 1964761Notes

Reaction equation

HRID 1964761 reaction equation
C1(N2CCOCC2)CCCC=1.[CH:12](=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15]C=1.Cl.[CH:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[CH:15](=[C:16]1[CH2:17][CH2:18][CH2:13][C:12]1=[O:19])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 4

HCID 240BenzaldehydeHCID 241BenzeneHCID 313Hydrochloric AcidHCID 702941-Morpholinocyclopentene

Product 1

HCID 2668132-PhenylmethylenecyclopentanoneYield 84.6%

Conditions

Temperature
30 °C

Procedure

With reflux device installed, 36.8 g (0.24 mol) of N-cyclopentenyl morpholine, 27.2 g (0.20 mol) of benzaldehyde and 200 mL of benzene were added to a round bottom flask and heated under reflux for 20 h. The resulting solution was cooled to 30° C., and slowing stirring while 62 mL of hydrochloric acid (6 mol/L) was added to the solution. After stirring for 2 h at room temperature, the benzene layer was separated and washed with water to neutral, and dried over anhydrous sodium sulfate overnight. Then the mixture was filtered and benzene was recovered by evaporation under reduced pressure. The residue was cooled and solidified, then recrystallized in cyclohexane/ethanol to yield 2-benzylidene-cyclopentanone with a yield of 84.6%.

Workup

  1. temperatureWith reflux device
  2. temperatureheated
  3. temperatureunder reflux for 20 h
  4. additionwas added to the solution
  5. customthe benzene layer was separated
  6. washwashed with water to neutral, and
  7. dry with materialdried over anhydrous sodium sulfate overnight
  8. filtrationThen the mixture was filtered
  9. custombenzene was recovered by evaporation under reduced pressure
  10. temperatureThe residue was cooled
  11. customrecrystallized in cyclohexane/ethanol

Sources & evidence

ORD record
ord-850b737d4a904ac7a4954ae3353b843c
Source dataset
uspto-grants-2013_04
Patent number
US08415505B2

Reaction notes

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