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

Participants

Reaction Conditions

Reaction Steps

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%

Provenance & Evidence