Ammonium Chloride → 1-(3-Cyclopentyloxy-4-methoxyphenyl)ethanol

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Reaction Steps

A solution of 3-cyclopentyloxy-4-methoxybenzaldehyde (10.00 g, 45.40 mM) in dry tetrahydrofuran (100 ml) was cooled to 0° C., then a tetrahydrofuran solution of methyl magnesium bromide (136.20 mM) was dropwise added to the solution and the mixture was stirred at that temperature for 2 hours. An aqueous ammonium chloride was added to the solution obtained, which was then warmed to room temperature and extracted with ethyl acetate, then the extract was successively washed with brine and water. The organic solution was dried over anhydrous magnesium sulfate, and the solvent was evaporated in vacuo to obtain a crude product of 1-(3-cyclopentyloxy-4-methoxyphenyl)ethanol (10.67 g) as a light yellow oil. The crude product thus obtained of 1-(3-cyclopentyloxy-4-methoxyphenyl)ethanol (10.67 g) was dissolved in dry methylene chloride (200 ml), manganese dioxide (39.2 g) was added to the solution, then the solution was vigorously stirred at room temperature for 16 hours. The undissolved material in the solution was removed by filtration through Celite, and the filtrate was concentrated in vacuo to obtain a residue as a yellow oil. The residue was purified by flash chromatography (SiO2: eluted with 25% ethyl acetate/hexane). The solvent was removed in vacuo and the resultant product was dried to obtain 3-cyclopentyloxy-4-methoxyacetophenone 10.00 g (yield 94.4%) as a yellow oil.

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