Methanol → Cyclohexanecarboxylic acid, 4-(hydroxymethyl)-, methyl ester

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Reaction Steps

To 4-hydroxymethylcyclohexanecarboxylic acid (TCI-JP, 0.50 g, 3.2 mmol) in 10 mL CH3OH was added 0.50 mL concentrated H2SO4. This mixture was warmed to reflux and allowed to stir for 2 h. The reaction mixture was then cooled and NH4OH was added until the solution tested basic using pH paper. The mixture was then extracted with 3×5 mL ethyl acetate. The combined organic extracts were washed with saturated, aqueous NaCl then were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to give 0.45 g of the title compound (0.26 mmol, 83% yield). MS (DCI/NH3) m/z 190 (M+NH4)+.

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