Acid-catalysed rearrangements of allyl 4-hydroxybenzoate and 3-methylbut-2- enyl-4-hydroxybenzoate

Department of Chemistry, Srikrishna College, Bagula-741 507, Nadia, West Bengal, India

E-mail : deysp2002@yahoo.co.in

Department of Chemistry, Chandidas Mahavidyalaya, Khujutipara-731 215, Birbhum, West Bengal, India

E-mail : deydk@yahoo.com

Manuscript received 27 June 2008, revised 31 December 2008, accepted 1 January 2009

On treatment with 75% polyphosphoric acid or TFA-H₂SO₄ (50%) allyl 4-hydroxybenzoate and 3-methylbut-2-enyl-4-hydroxybenzoate afforded 4-hydroxy-3-(2' -hydroxypropyl)benzoic acid and 4-hydroxy-3-(3' -hydroxy-3'- methylbutyl)benzoic acid, respectively. Mechanisms of these reactions are discussed.