Sulfuric Acid → 4-Butylphenol

Participants

Reaction Steps

A cold solution of sodium nitrite (28.95g, 0.419m) in water (90ml) was added in drops to a mixture of 4-n-butylaniline (60g, 0.402m), concentrated sulfuric acid (135g) and water (300ml) at 0°-5° C with stirring. After completion of addition the excess nitrous acid was tested with potassium iodide starch paper, and destroyed by the addition of urea. The resulting cold diazonium salt solution was slowly added to a boiling solution of water (210ml), sulfuric acid (375g) and anhydrous sodium sulfate (285g). The resulting reaction mixture was steam distilled. The distillate was collected until it became clear and saturated by adding sodium chloride. The resulting solution was extracted with ether and the combined ether extract were dried over anhydrous sodium sulfate. The solvent was evaporated and the residue was vacuum distilled to yield 4-n-butylphenol (44g, 73.3%), bp 106° C at 4.6 mm.

Provenance & Evidence