Chemistry · Ch 11 — Hydroxy Compounds and Ethers
Formation of Esters -- Schotten-Baumann Reaction
11.15.3
Formation of Esters -- Schotten-Baumann Reaction
Phenol reacts with acid chlorides (in the presence of NaOH/pyridine) to give esters; this acetylation/benzoylation of phenol is called the Schotten-Baumann reaction. With acetyl chloride: C6H5-OH + CH3-COCl gives CH3-COO-C6H5 (phenyl ethanoate) + HCl. With benzoyl chloride: C6H5-OH + C6H5-COCl gives C6H5-COO-C6H5 (phenyl benzoate) + HCl. The NaOH (or pyridine) present is not just a base catalyst but also mops up the HCl by-product as it forms, driving the otherwise reversible-looking acylation to completi …