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​​​​Acid mediated cyclodimerization of styrene oxide to 2-benzyl-4-phenyl-1,3-dioxalane; ​​​​acetal formation

SyntheticPage 312
DOI: 10.1039/SP312
Submitted Jul 10, 2009, published Jul 14, 2009
Ishmael Masesane (masesane@mopipi.ub.bw)
A contribution from Synthetic Group, Botswana


			Reaction Scheme: ​​​​Acid mediated cyclodimerization of styrene oxide to <SPAN class=csm-chemical-name id=csm1268840783711 title=2-benzyl-4-phenyl-1,3-dioxalane grpid="1">2-benzyl-4-phenyl-1,3-dioxalane</SPAN>

Chemicals Used

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

Procedure

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 %).

Author's Comments

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.

Data

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'').

Lead Reference

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

Other References

N/A

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