Styrene (Aldrich), MCPBA (Aldrich) Phosphoric acid (Aldrich)

Phosphoric acid (0.2 ml) was added drop-wise to styrene epoxide (0.5 g, 4.17 mmol) and the mixture was stirred at room temperature for 120 minutes. Saturated sodium bicarbonate (20 ml) was added and the mixture was extracted with dichloromethane (2 x 15 ml) and the organic fractions were combined, dried (magnesium sulphate) and concentrated under reduced pressure. The residue was subjected to flash chromatography eluting with petroleum ether/ethyl acetate (4:1) to give the product as a clear jelly (0.31 g, 61 %).

All reactions were performed under atmospheric pressure and all reagents were purchased from commercial sources and were used without further purification. The reaction is thought to proceed through a 1,2-hydride shift.

1H NMR (300 MHz, CDCl₃): 3.24 (2H, t, J = 5.7, PhCH₂), 3.75 (1H, dd, J = 7.8 Hz and 6.3 Hz, H-5), 4.22 (1H, dd, J = 7.8 Hz and 0.9 Hz, H-5), 5.06 (1H, t, J = 6.3 Hz and 0.9 Hz, H-4), 5.38 (1H, t, J = 5.7 Hz, H-2), 7.39-7.44 (10 H, m, Aromatic protons); 13C NMR (75 MHz, CDCl₃): 40.8 (PhCH₂), 72.0 (C-5), 78.5 (C-4), 105.4 (C-2), 126.4 (C-2'' and C-6''), 126.7 (C-4''), 128.1 (C-1'), 128.3 (C-3'' and C-5''), 128.5 (C-2' and C-6'), 130.0 (C-3' and C-5'), 136.0 (C-1'), 139.4 (C-1'').

Concellon, J. M.; Bernad, P. L.; de Solar, V.; Garcia-Granda, S.; Diaz, M. R. Adv. Synth. Catal. 2008, 350, 477 doi:10.1002/adsc.200700486

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