Ethanol → HCID 12512105, compound

HRID 1268195Notes

Reaction equation

HRID 1268195 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.[CH2:19](O)[CH3:20]>>[N+:1]([C:4]1[CH:12]=[C:8]([C:9]([O:11][CH2:19][CH3:20])=[O:10])[C:7]([OH:13])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 73185-Nitrosalicylic acid

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) at room temperature and the mixture was heated under reflux for 7.5 hours. After neutralization with aqueous sodium hydroxide, the reaction mixture was extracted with ethyl acetate. The extractant was washed with saturated aqueous sodium hydrogencarbonate, 0.5M hydrochloric acid and brine. The organic layer was dried over anhydrous magnesium sulfate, filtered and the filtrate concentrated in vacuo to give the desired compound (10.7 g, yield 85%) as a yellow solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 7.5 hours
  3. extractionAfter neutralization with aqueous sodium hydroxide, the reaction mixture was extracted with ethyl acetate
  4. washThe extractant was washed with saturated aqueous sodium hydrogencarbonate, 0.5M hydrochloric acid and brine
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-ff9f3b77eb1a46b897f35349adebff09
Source dataset
uspto-grants-2003_04
Patent number
US06555556B1

Reaction notes

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