Sodium Hydroxide → 2-Methylpropyl 2-[[(3-methoxyphenyl)thio]methyl]-6-methylbenzoate

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Reaction Steps

A 10N solution of sodium hydroxide (0.32 mL, 3.2 mmol) is added slowly to a solution of 3-methoxybenzenethiol (0.42 g, 3.0 mmol) in isobutanol (2 mL) followed by a solution of isobutyl 2-bromomethyl-6-methyl-benzoate (0.96 g, 3.3 mmol, example 2) in isobutanol (2 mL). The reaction is allowed to stir 15 min and is then partitioned between ethyl acetate and dilute aqueous HCl. The organic phase is washed with water, dried over magnesium sulfate, concentrated and purified by column chromatography (silica, 40% dichloromethane in hexanes) to provide the title compound. MS (EI) 344 (M)+.

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