Ethanol → Ethyl(9-Oxoxanthen-2-oxy)acetate

HRID 1464584Notes

Reaction equation

HRID 1464584 reaction equation
[O:1]=[C:2]1[C:15]2[CH:14]=[C:13]([O:16][CH2:17][C:18]([O-:20])=[O:19])[CH:12]=[CH:11][C:10]=2[O:9][C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.[OH-].[K+].O.[CH2:24](O)[CH3:25]>>[O:1]=[C:2]1[C:15]2[CH:14]=[C:13]([O:16][CH2:17][C:18]([O:20][CH2:24][CH3:25])=[O:19])[CH:12]=[CH:11][C:10]=2[O:9][C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2

Participants

5

Reactant 4

HCID 702EthanolHCID 962WaterHCID 14797Potassium HydroxideHCID 71959769-Oxoxanthen-2-oxyacetate

Product 1

HCID 15222242Ethyl(9-Oxoxanthen-2-oxy)acetate

Procedure

Ethyl (9-oxoxanthen-2-oxyacetate (10 g, 33 mmol) prepared as described above, was dissolved in 95% ethanol (150 mL), and 4 N aqueous KOH (30 mL, 0.12 mol) and water (15 mL) were added. The mixture was stirred for 35 minutes at 35°-40° C., cooled, and the solid precipitate which formed was collected by filtration, washed with absolute ether (3'20 mL), and air-dried. The structure of the potassium salt is shown below. Yield: 9.25 g (96%). TLC, Rf 0.90 [MeOH-H2O(4:1)]. NMR data in accordance with structure.

Workup

  1. temperaturecooled
  2. customthe solid precipitate which formed
  3. filtrationwas collected by filtration
  4. washwashed with absolute ether (3'20 mL), and
  5. customair-dried

Sources & evidence

ORD record
ord-905836dcef6d4dd1909f49728656744b
Source dataset
uspto-grants-1994_04
Patent number
US05306562

Reaction notes

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