Ethanol → 9-Oxo-9H-xanthene-3-carboxylic acid

HRID 1803336Notes

Reaction equation

HRID 1803336 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[C:9](=[O:19])[C:10]3[C:15]([O:16][C:17]=2[CH:18]=1)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[O:4].CCO>[OH-].[Na+]>[O:19]=[C:9]1[C:8]2[CH:7]=[CH:6][C:5]([C:3]([OH:4])=[O:2])=[CH:18][C:17]=2[O:16][C:15]2[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=2

Participants

4

Reactant 2

HCID 702EthanolHCID 473475Methyl 9-oxoxanthene-3-carboxylate2×

Product 1

HCID 4734739-Oxo-9H-xanthene-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A sample of 9-Oxo-9H-xanthene-3-carboxylic acid methyl ester, compound 4a, (16.6 g, 65.3 mmol) was suspended in 250 mL of 3 N NaOH and 250 mL of EtOH and heated to reflux for 1 h. At that time the EtOH was evaporated and the reaction was poured into 6 N HCl over ice and extracted with large volumes of 1:1 THF/diethyl ether. The combined organic phases were washed with brine, dried over magnesium sulfate, filtered and evaporated to provide 13.35 g of Compound 5a (55.6 mmol) after drying in a vacuum oven at 50° C. overnight.

Workup

  1. temperatureto reflux for 1 h
  2. customAt that time the EtOH was evaporated
  3. additionthe reaction was poured into 6 N HCl over ice
  4. extractionextracted with large volumes of 1:1 THF/diethyl ether
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-1cb345d5762c48f4830a56ae71d2aa1f
Source dataset
uspto-grants-2013_01
Patent number
US08350041B2

Reaction notes

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