4-Nitrophenol → 1-Nitro-4-(1,8-nonadiene-5-yloxy)benzene

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Reaction Steps

A 300 ml-capacity three neck flask containing a stirring bar and connected to a condenser was sufficiently dried. Then, a nitrogen atmosphere was established in the flask, and 1,8-nonadiene-5-ol (8) (3.72 g, 2.66 mmol), PPh3 (6.98 g, 2.66 mmol), and 4-nitrophenol (4.43 g, 3.19 mmol) were introduced into the flask. Dried THF (50 ml) was further added to the mixture, the mixture thus obtained was stirred at room temperature, DEAD (12.2 ml, 3.19 mmol) was then dropped into the flask, and the mixture thus obtained was stirred for 5 hours. When generation of ether was recognized by thin-layer chromatography (hexane:ethyl acetate=10:1), the solvent was distilled off under reduced pressure, the mixture was purified by flash chromatography on silica gel (hexane:ethyl acetate=10:1). Thus, 1-nitro-4-(1,8-nonadiene-5-yloxy)benzene (11) (4.731 g, 1.7 mmol, yield: 65%) was obtained as an intended compound. 1HNMR values of 1-nitro-4-(1,8-nonadiene-5-yloxy)benzene (11) are shown below.

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