Benzene → 2-[(4-Hydroxy-3-methoxyphenyl)methylidene]cyclopentan-1-one

HRID 1964772Notes

Reaction equation

HRID 1964772 reaction equation
C1(N2CC[O:9]CC2)CCCC=1.[OH:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][C:14]=1[O:21][CH3:22].Cl.[CH:24]1[CH:29]=[CH:28][CH:27]=[CH:26]C=1>>[OH:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[C:26]2[CH2:27][CH2:28][CH2:29][C:24]2=[O:9])=[CH:15][C:14]=1[O:21][CH3:22]

Participants

5

Reactant 4

HCID 241BenzeneHCID 313Hydrochloric AcidHCID 1183VanillinHCID 702941-Morpholinocyclopentene

Product 1

HCID 667487902-[(4-Hydroxy-3-methoxyphenyl)methylidene]cyclopentan-1-oneYield 92.6%

Conditions

Temperature
30 °C

Procedure

With reflux device installed, 36.8 g (0.24 mol) of N-cyclopentenyl morpholine, 0.20 mol of 4-hydroxy-3-methoxybenzaldehyde and 200 mL benzene were added to a round bottom flask and heated under refluxing 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 cyclohexan/ethanol to yield a light yellow flaky crystal product with a yield of 92.6%

Workup

  1. temperatureWith reflux device
  2. temperatureheated
  3. temperatureunder refluxing 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 cyclohexan/ethanol
  13. customto yield a light yellow flaky crystal product with a yield of 92.6%

Sources & evidence

ORD record
ord-390c0344eb2b4a11a2b12b19bb7d7bf5
Source dataset
uspto-grants-2013_04
Patent number
US08415505B2

Reaction notes

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