Benzene → HCID 54450319, compound

HRID 1964759Notes

Reaction equation

HRID 1964759 reaction equation
C1(N2CC[O:9]CC2)CCCC=1.[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=1.Cl.[CH:22]1[CH:27]=[CH:26][CH:25]=[CH:24]C=1>>[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[C:24]2[CH2:25][CH2:26][CH2:27][C:22]2=[O:9])=[CH:15][CH:14]=1

Participants

5

Reactant 4

HCID 241BenzeneHCID 313Hydrochloric AcidHCID 77264-ChlorobenzaldehydeHCID 702941-Morpholinocyclopentene

Product 1

HCID 54450319HCID 54450319, compoundYield 66.3%

Conditions

Temperature
30 °C

Procedure

With reflux device installed, 36.8 g (0.24 mol) of N-cyclopentenyl morpholine, 28.1 g (0.20 mol) of p-chlorobenzaldehyde 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 slowly stirred while 62 mL of hydrochloric acid (6 mol/L) was added. 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 to remove anhydrous sodium sulfate, and benzene was recovered by evaporation under reduced pressure. The residue was cooled and solidified, then recrystallized in 95% ethanol to yield 32.9 g of light yellow flaky crystal product with a yield of 66.3%.

Workup

  1. temperatureWith reflux device
  2. temperatureheated
  3. temperatureunder reflux for 20 h
  4. additionwas added
  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. customto remove anhydrous sodium sulfate, and benzene
  10. customwas recovered by evaporation under reduced pressure
  11. temperatureThe residue was cooled
  12. customrecrystallized in 95% ethanol

Sources & evidence

ORD record
ord-8f707392f0854b7a94d64980b4d2fd92
Source dataset
uspto-grants-2013_04
Patent number
US08415505B2

Reaction notes

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