[[4-[[2-(1-Methylethoxy)ethoxy]methyl]phenoxy]methyl]oxirane

Chemical Properties

Pale Yellow Oil

Uses

An intermediate for the synthesis of Bisoprolol.

Synthesis

The synthesis of 4-[[2-(1-Methylethoxy)ethoxy]methyl]phenoxy]methyl]oxirane is as follows: steps. 1) Preparation of 4-hydroxybenzyl alcohol: 4-Hydroxybenzaldehyde is reduced with NaBH4. Work-up yields the product. 2) Preparation of 4-[(2-isopropoxyethoxy)methyl]phenol: 4-Hydroxybenzyl alcohol reacts with 2-isopropoxyethanol catalyzed by Amberlyst-15 resin. Work-up gives the product. 3) Preparation of the title oxirane derivative: The sodium salt of the phenol from step 2 reacts with epichlorohydrin. Toluene extraction is performed. The organic phase is treated with solid NaOH, washed, and distilled to an oil. High-vacuum distillation purifies the product.