Hydrochloric Acid → Benzoic acid, 2-hydroxy-, 3-(hydroxymethyl)phenyl ester

To a solution of Compound 5 (9.4 g, 0.024 mol) in THF (120 ml) was added a solution of hydrochloric acid (HCl) (100 ml, 6 N HCl in water) at RT. The reaction mixture was stirred at RT for 2 days. Then, the reaction mixture was mixed with EtOAc (300 ml) and the resulting layers were separated. The organic layer was washed with aqueous saturated NaHCO3 (3×100 ml) and brine (1×100 ml). The aqueous layer was neutralized to pH 7 with aqueous saturated NaHCO3, and extracted with EtOAc (2×100 ml). These EtOAc extracts were combined and washed with brine (1×100 ml). Then, all the organic layers were combined and dried over anhydrous Na2SO4. The crude product obtained upon concentration was purified by column chromatography (elution solvent: 30% EtOAc in hexanes) to yield 5.0 g of Compound 6 in 87% yield.

1. customthe resulting layers were separated
2. washThe organic layer was washed with aqueous saturated NaHCO3 (3×100 ml) and brine (1×100 ml)
3. extractionextracted with EtOAc (2×100 ml)
4. washwashed with brine (1×100 ml)
5. dry with materialdried over anhydrous Na2SO4
6. customThe crude product obtained upon concentration
7. customwas purified by column chromatography (elution solvent: 30% EtOAc in hexanes)

ORD record

ord-9d9517d373834c02939fd1c8738883a8

Source dataset

uspto-grants-2003_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06538033B2