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Phenyl-2-Propanol from Styrene Oxide

Zh. Org. Khim. 28(7), 1377-9 (1992)

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Grignard reagentTimeProduct
Yield
PrMgCl
20 min
PhCHClCH2OH
72%
MeMgBr
20 min
PhCHBrCH2OH
83%
EtMgBr
20 min
PhCHBrCH2OH
75%
MeMgI
20 min
PhCHICH2OH/PhCH(OH)CH2I
90%
MeMgBr
6 h
PhCH2CH(OH)CH3
80%
EtMgBr
6 h
PhCH2CH(OH)Et
65%
PhMgBr
6 h
PhCH2CH(OH)Ph
84%
MeMgI
24 h
PhCH(OH)CH2I
60%

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).