2-(6-Hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acid → HCID 19609083, compound

Participants

Reaction Steps

To a solution of 50 mg (0.15 mmol) of fluorescein in 0.3 mL of methanesulfonic acid was added 13 μL (0.16 mmol) of chloromethyl methyl ether at room temperature. The mixture was stirred at room temperature for 48 hours. The reaction mixture was poured into 10 mL of ice-cold water. A yellow-orange solid precipitated out and was filtered. The crude product was purified by preparative thin layer chromatography (silica gel, 2 mm) using 8:1:1 chloroform:methanol:toluene to yield 20 mg (37%) of rac-4'-(hydroxymethyl)-3',6'-dihydroxyspiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one (2). NMR, IR and MS data confirmed the identity of the compound. To confirm the structural identity of compound (2), the compound was derivatized to the corresponding triacetate. NMR and MS data confirmed the identity of the triacetate. Hydrolysis of the triacetate yielded compound (2).

Provenance & Evidence