Sulfuric Acid → Anthroxanic acid

HRID 1742545Notes

Reaction equation

HRID 1742545 reaction equation
S(=O)(=O)(O)O.[N+:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][C:16]([OH:18])=[O:17])([O-])=[O:7]>>[N:6]1[O:7][C:15]([C:16]([OH:18])=[O:17])=[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=12

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 77337(2-Nitrophenyl)acetic acid

Product 1

HCID 258162Anthroxanic acidYield 50.4%

Procedure

To 1 l of concentrated sulfuric acid, 40 g (0.22 mol) of orthonitrophenylacetic acid were added, followed by stirring at 105°-110° C. for 90 minutes. After cooling, 2.5 l of ice water in limited amounts was added to the reaction mixture. The resultant mixture was extracted with 1 l of ethyl ether. The extract was dried over anhydrous sodium sulfate and the solvent was distilled off, so that 18.1 g (yield: 50.2%) of 2,1-benzisoxazole-3-carboxylic acid was obtained as crystals.

Workup

  1. temperatureAfter cooling
  2. extractionThe resultant mixture was extracted with 1 l of ethyl ether
  3. dry with materialThe extract was dried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-4546494c9acb47928f37b3ccaa56cb6a
Source dataset
uspto-grants-1994_08
Patent number
US05338857

Reaction notes

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