Epichlorohydrin → 1-(2,3-Epoxypropoxy)-5,8-dihydronaphthalene

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Reaction Steps

To a cooled solution of 15 g. (0.1 m.) of 5,8-dihydro-1-naphthol and 13.2 g. (0.14 m.) of epichlorohydrin in 38 ml. of p-dioxane, a cold solution of 4.9 g. of sodium hydroxide in 10 ml. of water is added dropwise. The mixture is refluxed three hours, cooled, and extracted with benzene. The benzene extract is washed with water, dried (MgSO4) and evaporated in vacuo to give 1-(2,3-epoxypropoxy)-5,8-dihydronaphthalene. Distillation of the crude oil at 1.2 mm., b.p. 139°-140°, gives a colorless liquid; λliq.max. film 1250, 910, 840 cm-1 (characteristic epoxy bands), CDCl3 4.13 (-C/H=C/H-), 2.5 - 3.5 (aromatic protons).

Provenance & Evidence