Hydrogen Bromide → HCID 178447572, compound

Participants

Reaction Steps

A mixture of 3- and 4-bromocyclohexanols (3.6 g, 20 mmol)(the mixture of 3- and 4-bromocyclohexanols was obtained by treating 1,4-cyclohexanediol with hydrobromic acid (48 wt % in water) under reflux followed by conventional treatments) was treated with pivaloyl chloride (3.7 mL, 30 mmol) in pyridine (50 mL), which was then stirred at room temperature for 4 hours. After evaporation in vacuum, the crude mixture was purified by silica gel chromatography (hexane/ethyl acetate=20/1) to give 3-bromocyclohexyl pivaloate (trans/cis=33/67, 0.63 g, 12%) and trans-4-bromocyclohexyl pivaloate (0.79 g, 15%) as colorless oily substances.

Provenance & Evidence