4-Hydroxybenzaldehyde → Methyl 2-(4-formylphenoxy)acetate

Participants

Reaction Steps

A solution of 4-hydroxy benzaldehyde, (1.22 g, 0.01 m), methyl glycolate (0.97 g, 0.01 m), and triphenylphosphine, (3.93 g, 0.015 m), in dry tetrahydrofuran, (50 ml) was stirred with cooling in ice and diethylazodicarboxylate, (2.61 g, 0.015 m), added dropwise. The solution was stirred at room temperature for 0.5 hours, then evaporated in vacuo to dryness. Column chromatography of the residue on silica gel eluting with chloroform yielded 1.30 g (67%) of the title compound as an oil which crystallized on standing, mp 39°-41° C., νmax (mull) 1750, 1680, 1595, 1575, 1505 cm-1.

Provenance & Evidence