3-[(4-methylphenyl)methoxy]benzaldehyde

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture comprising triphenyl[4-(piperidinomethyl)benzyl]phosphonium bromide (1.06 g) and THF (10 ml) was added dropwise under a nitrogen atmosphere a 1.6 M solution of butyllithium in hexane (1.28 ml), and the resulting mixture was stirred for 30 minutes. To this reaction mixture was added 3-(4-methylbenzyloxy)benzaldehyde (453 mg), and the resulting mixture was stirred at room temperature for one hour, was then mixed with water (100 ml) and was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated solution of sodium chloride, was dried with anhydrous sodium sulfate and was then evaporated under reduced pressure to remove the solvent. The resulting residue was subjected to purification using column chromatography (ethyl acetate/triethylamine=20/1) and to recrystallization to obtain (E)-1-[4-[3-(4-methylbenzyloxy)styryl]benzyl]piperidine (compound 97) (330 mg) as colorless crystals. the resulting mixture was stirred at room temperature for one hour was extracted with ethyl acetate The organic layer was washed with an aqueous saturated solution of sodium chloride was dried with anhydrous sodium sulfate was then evaporated under reduced pressure to remove the solvent The resulting residue was subjected to purification to recrystallization

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 3-hydroxybenzaldehyde (5.00 g) dissolved in acetone (70 ml) were added 4-methylbenzyl chloride (6.51 ml), potassium carbonate (8.49 g) and sodium iodide (7.36 g), and the resulting mixture was heated at reflux for 24 hours and was then evaporated under reduced pressure to remove the solvent. The residue was mixed with water (200 ml) and was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated solution of sodium chloride was dried with anhydrous sodium sulfate, and was then evaporated under reduced pressure to remove the solvent. The thus-obtained residue was subjected to purification using column chromatography (ethyl acetate/hexane=1/10) to obtain 3-(4-methylbenzyloxy)benzaldehyde (7.86 g) as a colorless oily substance. the resulting mixture was heated at reflux for 24 hours was then evaporated under reduced pressure to remove the solvent The residue was mixed with water (200 ml) was extracted with ethyl acetate The organic layer was washed with an aqueous saturated solution of sodium chloride was dried with anhydrous sodium sulfate was then evaporated under reduced pressure to remove the solvent The thus-obtained residue was subjected to purification