Benzene → HCID 67064430, compound

HRID 1964763Notes

Reaction equation

HRID 1964763 reaction equation
C1(N2CC[O:9]CC2)CCCC=1.[CH3:12][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>>[CH3:12][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 77254-MethylbenzaldehydeHCID 702941-Morpholinocyclopentene

Product 1

HCID 67064430HCID 67064430, compoundYield 94.5%

Conditions

Temperature
30 °C

Procedure

With reflux device installed, 36.8 g (0.24 mol) of N-cyclopentenyl morpholine, 24.0 g (0.20 mol) of 4-methylbenzaldehyde 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 and benzene was recovered by evaporation under reduced pressure. The residue was cooled and solidified, then recrystallized in cyclohexane/ethanol to yield light yellow flaky crystal product with a yield of 94.5%.

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. custombenzene was recovered by evaporation under reduced pressure
  10. temperatureThe residue was cooled
  11. customrecrystallized in cyclohexane/ethanol
  12. customto yield light yellow flaky crystal product with a yield of 94.5%

Sources & evidence

ORD record
ord-b765e035fa9d4ad1903181a9f2d21959
Source dataset
uspto-grants-2013_04
Patent number
US08415505B2

Reaction notes

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