Pentaerythritol → 2,2-Bis(hydroxymethyl)propane-1,3-diyl dibutyrate

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Reaction Steps

In this example, pentaerythritol tributyrate, the tributyl ester of pentaerythritol, was synthesized from pentaerythritol and butyryl chloride as follows. To a solution of pentaerythritol (0.99 g, 7.28mmol) in dry pyridine (50 mL, under argon) at 0° C. was added butyryl chloride (2.3 mL, 22 mmol, 3 equiv) dropwise over one hour. The ice bath was removed after one hour, and the reaction stirred 24 hours at room temperature. Water (7 mL) was added and the bulk of pyridine was removed on the rotary evaporator at 2 Torr. The residue was dissolved in 1N HCL (12 mL) and the pentaerythritol esters extracted with CHCl3 (3×20 mL). The combined organic extracts were dried (MGSO4) and concentrated under vacuum to an oil (2.73 g). Purification by flash column chromatography using silica gel afforded the desired triester pentaerythritol tributyrate (1.34 g; 53%) as well as pentaerythritol dibutyrate (0.51 g; 26%) and pentaerythritol tetrabutyrate (0.42 g; 14%).

Provenance & Evidence