Phenyl-2-Propanol from Styrene Oxide

Zh. Org. Khim. 28(7), 1377-9 (1992)
[ Back to the Chemistry Archive ]

Experimental part

To a vigorously stirring solution of styrene oxide (2.4 g) and titanium(IV)isopropoxide (5.7 g) in 100 ml of absolute ether, Grignard reagent (20 ml of 1N solution in ether) was added at room temperature during 15-20 min. The reaction mixture was stirred for time showed in the table and decomposed with 5% sulfuric acid. Two phases was obtained. The organic phase was separated, washed with brine and dried over MgSO4. The solvent was evaporated, and the residue purified by column chromatography (silicagel L100/250, Et2O-hexane 1:3)

Grignard reagentTimeProductYield
PrMgCl20 minPhCHClCH2OH72%
MeMgBr20 minPhCHBrCH2OH83%
EtMgBr20 minPhCHBrCH2OH75%
MeMgBr6 hoursPhCH2CH(OH)CH380%
EtMgBr6 hoursPhCH2CH(OH)Et65%
PhMgBr6 hoursPhCH2CH(OH)Ph84%
MeMgI24 hoursPhCH(OH)CH2I60%