Hexamethylenetetramine → 2-Hydroxy-5-(5-trifluoromethyl-tetrazol-1-yl)benzaldehyde

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Reaction Steps

A solution of 4-(5-trifluoromethyl-tetrazol-1-yl)-phenol (45 mmol) in trifluoroacetic acid (200 ml) and hexamethylenetetramine (186.9 mmol) was heated at 100°, under nitrogen for 16 h. The reaction mixture was quenched with 2N sulphuric acid (250 ml) and extracted with ether (3×250 ml)). The combined organics were dried (Na2SO4) and evaporated to give a dark yellow oil. Purification by FCC (hexane/ether (2:1)) afforded the title compound (8.8 g) as a pale yellow solid. T.I.c. (hexane/ether (2:1)) Rf 0.36

Provenance & Evidence