Sulfuric Acid → Anthroxanic acid

HRID 1450663Notes

Reaction equation

HRID 1450663 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 if 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 if of ethyl ether
  3. dry with materialThe extract was dried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-a257615599c0495a82bb4a4f1e0bba37
Source dataset
uspto-grants-1997_02
Patent number
US05602160

Reaction notes

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