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

HRID 1603234Notes

Reaction equation

HRID 1603234 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]([C:23]([OH:25])=[O:24])=[C:5]([C:7]2[C:17]3[CH:18]=[CH:19][C:20]([OH:22])=[CH:21][C:16]=3[O:15][C:14]3[C:8]=2[CH:9]=[CH:10][C:11]([CH:13]=3)=[O:12])[CH:6]=1.[CH3:26][O:27]CCl>CS(O)(=O)=O>[OH:27][CH2:26][C:13]1[C:14]2[O:15][C:16]3[C:17](=[CH:18][CH:19]=[C:20]([OH:22])[CH:21]=3)[C:7]3([C:5]4[C:4](=[CH:3][CH:2]=[CH:1][CH:6]=4)[C:23](=[O:25])[O:24]3)[C:8]=2[CH:9]=[CH:10][C:11]=1[OH:12]

Participants

4

Reactant 2

HCID 33832-(6-Hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acidHCID 7864Chloromethyl Methyl Ether

Product 1

HCID 19609083HCID 19609083, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Procedure

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).

Workup

  1. customA yellow-orange solid precipitated out and
  2. filtrationwas filtered
  3. customThe crude product was purified by preparative thin layer chromatography (silica gel, 2 mm)

Sources & evidence

ORD record
ord-e61db3e250884eb39ada3aafd6c9f138
Source dataset
uspto-grants-1999_11
Patent number
US05986094

Reaction notes

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