Monobenzone → ((p-(Benzyloxy)phenoxy)methyl)oxirane

Participants

Reaction Steps

Alkylation of 4-(benzyloxy)phenol with 2-(bromomethyl)oxirane (76) as in Example 2A, followed by chromatography of the product on silica gel, eluting with 0-25% CH2Cl2/petroleum ether (foreruns) and then with 25% CH2Cl2/petroleum ether, gave 2-{[4-(benzyloxy)phenoxy]methyl}oxirane (78) (reported by Kopka et al., 2003 using epichlorohydrin) (79%) as a white solid: mp (CH2Cl2/pentane) 61-62° C.; 1H NMR (CDCl3) δ 7.44-7.28 (m, 5H), 6.90 (dt, J=9.3, 2.8 Hz, 2H), 6.85 (dt, J=9.3, 2.8 Hz, 2H), 4.16 (dd, J=11.1, 3.3 Hz, 1H), 3.92 (dd, J=11.1, 5.6 Hz, 1H), 3.32 (m, 1H), 2.89 (dd, J=4.8, 4.3 Hz, 1H), 2.73 (dd, J=5.0, 2.7 Hz, 1H).

Provenance & Evidence