Sulfuric Acid → 7-Nitrobenzofuran-3(2H)-one

HRID 440672Notes

Reaction equation

HRID 440672 reaction equation
[N+:1]([C:4]1[C:12]2[O:11][CH:10](C(OCC)=O)[C:9](=[O:18])[C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH-].[Na+].S(=O)(=O)(O)O>>[N+:1]([C:4]1[C:12]2[O:11][CH2:10][C:9](=[O:18])[C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 22404730Ethyl 2,3-dihydro-7-nitrobenzofuran-3-on-2-ylcarboxylate

Product 1

HCID 224047597-Nitrobenzofuran-3(2H)-one

Procedure

In a flask 3.77 g (0.015 mole) of ethyl 2,3-dihydro-7-nitrobenzofuran-3-on-2-ylcarboxylate is suspended in 75 mL of a 5% aqueous solution of sodium hydroxide which is heated at reflux until all solid has gone into solution. The solution is cooled to ambient temperature, and dilute sulfuric acid is added cautiously until there is no further evidence of decarboxylation. The product is extracted with ethyl acetate, and the combined extracts are dried over anhydrous magnesium sulfate and filtered. The filtrate is evaporated under reduced pressure, leaving 2,3-dihydro-7-nitro-3-benzofuranone as a residue.

Workup

  1. temperatureis heated
  2. temperatureat reflux until all solid
  3. extractionThe product is extracted with ethyl acetate
  4. dry with materialthe combined extracts are dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe filtrate is evaporated under reduced pressure

Sources & evidence

ORD record
ord-ae92de2aaec94a80a92b0831b3386e8d
Source dataset
uspto-grants-1996_05
Patent number
US05521147

Reaction notes

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