Ethanol → HCID 12512105, compound

HRID 1796210Notes

Reaction equation

HRID 1796210 reaction equation
[N+:1]([C:4]1[CH:12]=[C:8]([C:9]([OH:11])=[O:10])[C:7]([OH:13])=[CH:6][CH:5]=1)([O-:3])=[O:2].S(=O)(=O)(O)O.[OH-].[Na+].[CH2:21](O)[CH3:22]>>[N+:1]([C:4]1[CH:12]=[C:8]([C:9]([O:11][CH2:21][CH3:22])=[O:10])[C:7]([OH:13])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 73185-Nitrosalicylic acidHCID 14798Sodium Hydroxide

Product 1

HCID 12512105HCID 12512105, compoundYield 85%

Procedure

To a solution of 5-nitrosalicylic acid (10.8 g) in ethanol (100 ml) was added concentrated sulfuric acid (92.0 g) with stirring at room temperature, and the resulting mixture was refluxed for 7.5 hours. After cooling to room temperature, the reaction mixture was neutralized with an aqueous sodium hydroxide solution and extracted with ethyl acetate. The extract was washed successively with a saturated aqueous sodium hydrogencarbonate solution, 0.5N hydrochloric acid and a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and evaporated in vacuo to afford the title compound (10.7 g, yield: 85%) as a pale yellow solid.

Workup

  1. temperaturethe resulting mixture was refluxed for 7.5 hours
  2. temperatureAfter cooling to room temperature
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed successively with a saturated aqueous sodium hydrogencarbonate solution, 0.5N hydrochloric acid
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-4ea05a70d4a84b79a8d79cab0201f978
Source dataset
uspto-grants-2006_04
Patent number
US07030138B2

Reaction notes

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