Ethanol → Ethyl alpha-nitro-9H-xanthene-9-acetate

HRID 1769542Notes

Reaction equation

HRID 1769542 reaction equation
O[CH:2]1[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:9][C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.[N+:16]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])([O-:18])=[O:17].[OH-].[K+].C(O)C>O>[N+:16]([CH:19]([CH:2]1[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:9][C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:20]([O:22][CH2:23][CH3:24])=[O:21])([O-:18])=[O:17]

Participants

6

Reactant 4

HCID 702EthanolHCID 14797Potassium HydroxideHCID 69379Ethyl nitroacetateHCID 72861Xanthydrol

Product 1

HCID 15290758Ethyl alpha-nitro-9H-xanthene-9-acetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

9-Hydroxyxanthene (9.9 g, 50 mmol) and ethyl nitroacetate (6.1 mL, 55 mol) are mixed and heated at 100° C. (oil bath) for 1.5 hours. After cooling, a waxy mixture is suspended in 40 mL of absolute alcohol and 40 mL of 1.25M of ethanolic potassium hydroxide solution is added. The solution is stirred for 45 minutes at room temperature and ethanol is stripped off. The remaining solid is suspended in water and extracted with diethyl ether. The aqueous portion is acidified with 85% phosphoric acid to pH 2 to 3 to give a white suspension which is cooled overnight. The precipitate is collected by filtration and dried in a vacuum oven at 50° C. This gives 9.18 g of the title compound as a white solid; mp 89°-91° C.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with diethyl ether
  3. customto give a white suspension which
  4. temperatureis cooled overnight
  5. filtrationThe precipitate is collected by filtration
  6. customdried in a vacuum oven at 50° C

Sources & evidence

ORD record
ord-327004b003b141acbb54bf419399cd8d
Source dataset
uspto-grants-1995_01
Patent number
US05380925

Reaction notes

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