Epichlorohydrin → HCID 54348861, compound

Participants

Reaction Steps

Potassium tert.butoxide (1.347 g, 12.00 mmol) is added to a solution of methylene di(p-hydroxybenzoate) (1.728 g, 6.00 mmol) prepared as described in Example 15 in DMF (75 ml), under a dry N2 atmosphere. Epichlorohydrin (2.22 g, 24.00 mmol) is added and after 24 hours at 20° C. the solvent is removed under reduced pressure. The residue is dissolved by adding dichloromethane (75 ml) and water (30 ml) and adjusting the pH to neutral using hydrochloric acid (1M). After separating the phases the dichloromethane layer is washed with water (3×30 ml). The organic phase is dried (MgSO4) and the solvent removed under reduced pressure to give 1.22 g (51%) product as a colourless oil. 1H NMR (60 MHz, CDCl3): δ 2.8 (4H, m, 2×epoxy--CH2), 3.3 (2H, m, 2×epoxy--CH), 4.05 (2H, dd, J=22, 11 Hz, 2×O--CH--H), 4.12 (2H, dd, J=22, 11 Hz, 2×O--CH--H), 6.14 (2H, s, O--CH2 --O), 6.9 (4H, m, 2×Ar), 7.9 (4H, m, 2×Ar).

Provenance & Evidence