4-Hydroxy-2-methylbenzenesulfonic acid synthesis

Yield:132281-59-5 23%

Reaction Conditions:

Stage #1: 3-methyl-phenolwith sulfuric acid at 100;Inert atmosphere;
Stage #2: with sodium carbonate in water; pH=14;Inert atmosphere;

Steps:

General procedure: m-cresol (50g, 463 mmol) was dissolved in H₂SO₄ (35 mL) and heated to 100^oC overnight. The mixture was diluted by H2O and pH was basified topH14 using a saturated solution of Na₂CO₃. The mixture was washed with ethyl acetate, the aqueous phase was concentrated. The white powder was dissolved in EtOH and stirred for 20h, the solid was filtered,and the organic phase was concentrated to give sodium 4-hydroxy-2-methylbenzenesulfonate (20g, 23%) as white solid.

References:

Boiteau, Jean-Guy;Ouvry, Gilles;Arlabosse, Jean-Marie;Astri, Stéphanie;Beillard, Audrey;Bhurruth-Alcor, Yushma;Bonnary, Laetitia;Bouix-Peter, Claire;Bouquet, Karine;Bourotte, Marilyne;Cardinaud, Isabelle;Comino, Catherine;Deprez, Beno?t;Duvert, Denis;Féret, Angélique;Hacini-Rachinel, Feriel;Harris, Craig S.;Luzy, Anne-Pascale;Mathieu, Arnaud;Millois, Corinne;Orsini, Nicolas;Pascau, Jonathan;Pinto, Artur;Piwnica, David;Polge, Ga?lle;Reitz, Arnaud;Reversé, Kevin;Rodeville, Nicolas;Rossio, Patricia;Spiesse, Delphine;Tabet, Samuel;Taquet, Nathalie;Tomas, Lo?c;Vial, Emmanuel;Hennequin, Laurent F. [Bioorganic and Medicinal Chemistry,2018,vol. 26,# 4,p. 945 - 956] Location in patent:supporting information