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

HRID 258187
Notes
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Reaction equation

HRID 258187 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 1.25 M 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-0ae9fb3e0f2140cf8791a86601f25eb2
Source dataset
uspto-grants-1993_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05264577

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes