Benzene → HCID 53672316, compound

HRID 1964766Notes

Reaction equation

HRID 1964766 reaction equation
C1(N2CC[O:9]CC2)CCCC=1.[Br: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>>[Br: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 702941-MorpholinocyclopenteneHCID 707414-Bromobenzaldehyde

Product 1

HCID 53672316HCID 53672316, compound

Conditions

Temperature
30 °C

Procedure

With reflux device installed, 36.8 g (0.24 mol) of N-cyclopentenyl morpholine, 0.20 mol of 4-bromobenzaldehyde 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 a light yellow flaky crystal product with a recovery of 71.2%.

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 a light yellow flaky crystal product with a recovery of 71.2%

Sources & evidence

ORD record
ord-7e3f4e75e4114ee0b12ba6c80684119c
Source dataset
uspto-grants-2013_04
Patent number
US08415505B2

Reaction notes

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