Acid hydrolysis of an acetonide; diols
Submitted Aug 23, 2001, published Aug 23, 2001
The acetonide (12.51g, 49.6mmol) is stirred in methanol (43mL) at room temperature and the HCl (4.3mL) is added. The reaction is stirred until completion (TLC, 7-8 hours) then carefully quenched with sodium bicarbonate solution, extracted 6 times with ether, washed with brine, dried over magnesium sulphate, filtered and concentrated in vacuum to give an off white solid. Purification can be by column chromatography eluting with 35-100% EtOAc/PE or more conveniently by recrystallisation using 1:1 EtOAc/PE to yield about 10g (90-95%) of white solid.
1H NMR (300MHz, CH3OD) 4.52 (1H, m), 3.66 (2H, m).
Hirama M., Iguchi S., Xing G. J. Org. Chem. 2001, 66, 2146.
Keywords: diol, hydrolysis, acid hydrolysis, acetonide, 125