HCID 14919052, compound → Ethyl 2-hydroxy-4-(methylsulfonyl)benzoate

Participants

Reaction Conditions

Reaction Steps

A mixture of 10 (15 g) and pyridinium hydrochloride (45 g) was heated under an inert atmosphere at 180° C. for 1.5 h and cooled. The mixture was partitioned between EtOAc and aqueous HCl (5%). The organic layer was washed with aqueous HCl (5%), dried, filtered, and concentrated. A solution of the resulting residue in EtOH (400 mL) was treated with concentrated H2SO4 (10 mL) and heated overnight at 75° C. After cooling, the mixture was concentrated and partitioned between EtOAc and saturated aqueous NaHCO3. The organic layer was extracted with 1 M NaOH (4 times). This combined aqueous layer was brought to acidic pH by addition of aqueous HCl (5%) and was extracted with EtOAc. This organic layer was dried (MgSO4), filtered, and evaporated giving 8.5 g of 2-hydroxy-4-methanesulfonyl-benzoic acid ethyl ester 11 as a solid.

Provenance & Evidence