Methanol → HCID 15718093, compound

HRID 1110084Notes

Reaction equation

HRID 1110084 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[C:11]1[CH:10]=[C:9]([C:17]([OH:19])=[O:18])[CH:8]=[CH:7][C:6]=1[O:5]2.S(=O)(=O)(O)O.[CH3:25]O>>[CH3:25][O:18][C:17]([C:9]1[CH:8]=[CH:7][C:6]2[O:5][C:4]3[C:13](=[CH:14][CH:15]=[C:2]([OH:1])[CH:3]=3)[C:12](=[O:16])[C:11]=2[CH:10]=1)=[O:19]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 15718089HCID 15718089, compound

Product 1

HCID 15718093HCID 15718093, compoundYield 97%

Procedure

A mixture of 6-hydroxy-9-oxo-9H-xanthene-2-carboxylic acid (Gapinski, D. M. "Leukotriene Antagonists", U.S. Pat. No. 4,996,230, which is incorporated herein by reference, 1991; 10.6 g, 41.4 mmol) and concentrated sulfuric acid (1 mL) in methanol (100 mL) was refluxed for 48 hours. The mixture was cooled to room temperature and the resulting precipitate collected by vacuum filtration. The filtrate was concentrated in vacuo and diluted with water, which resulted in additional precipitate. This was collected and combined with the first fraction to provide 10.8 g (97%) of the title product: 1H-NMR (DMSO-d6) 11.03 (s, 1H, --OH), 8.56 (d, J=2 Hz, 1H), 8.18 (dd, J=9, 2 Hz, 1H), 7.96 (d, J=9 Hz, 1H), 7.59 (d, J=9 Hz, 1H), 6.88 (dd, J=9, 2 Hz, 1H), 6.81 (d, J=2 Hz, 1H), 3.86 (s, 3H); MS-FAB (m/e) 271 (p+1, 6); IR (KBr, cm-1) 3093 (b), 1727, 1604, 1459, 1282, 1120, 767. Anal. (C15H10O5 :

Workup

  1. filtrationthe resulting precipitate collected by vacuum filtration
  2. concentrationThe filtrate was concentrated in vacuo
  3. additiondiluted with water, which
  4. customresulted in additional precipitate
  5. customThis was collected

Sources & evidence

ORD record
ord-7693a3c1d8624ec8a8321df1124d0763
Source dataset
uspto-grants-1994_06
Patent number
US05324743

Reaction notes

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