Application
1,6-Diacetoxyhexane, also known as hexanediol diacetate, can be prepared from 3-bromopropylacetate. Literature reports that it can be used to prepare the fungicide 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid.
Synthesis
3-Bromopropyl acetate (453 mg, 2.50 mmol) was added to a solution of CoBr2 (10 mol%, 0.25 mmol, 55 mg) and manganese powder (3.8 eq, 9.5 mmol, 500 mg) in CH3CN (3 mL) at room temperature. The manganese powder was activated with a trace amount of trifluoroacetic acid (50 L) and stirred at room temperature for 5 min until the fumes disappeared. Pyridine (0.5 mL) was added and stirred at 50C for 3-6 hours. Quench by adding 2MHCl (30mL) solution. The solution was extracted with Et2O or EtOAc (3x50 mL), dried over MgSO4, filtered and concentrated in vacuum. 1,6-Diacetoxyhexane was purified by rapid chromatography on silica gel.
