Sulfuric Acid → 3-Oxo-1,3-dihydro-2,1-benzoxazole-5,7-dicarboxylic acid

HRID 2049909

Reaction equation

HRID 2049909 reaction equation
[N+:1]([C:4]1[C:12]([C:13]([OH:15])=[O:14])=[CH:11][C:10]([C:16]([OH:18])=[O:17])=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])([O-])=O.[Mn]([O-])(=O)(=O)=O.[K+].[N+](C1C(C)=CC(C)=CC=1C)([O-])=O.S(=O)(=O)(O)O>[Zn].C(OCC)(=O)C.O>[C:16]([C:10]1[CH:9]=[C:5]([C:6]([OH:8])=[O:7])[C:4]2[NH:1][O:14][C:13](=[O:15])[C:12]=2[CH:11]=1)([OH:18])=[O:17]

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 690512-NitromesityleneHCID 516875Potassium PermanganateHCID 32590422-nitrobenzene-1,3,5-tricarboxylic Acid

Product 1

HCID 134113503-Oxo-1,3-dihydro-2,1-benzoxazole-5,7-dicarboxylic acid

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 12.8 g. of nitrotrimesic acid (prepared by alkaline potassium permanganate oxidation of nitromesitylene) in 200 ml. of water containing 30 g. of sulfuric acid are added 6.5 g. of zinc dust in portions at such a rate so as to maintain a temperature of about 25° C. After the addition, the mixture is stirred for an additional 1 hr. After this time, 200 ml. of ethyl acetate are added and the mixture is rapidly stirred for 15 min. The reaction is then filtered by suction through a pad of filter aid. The organic layer is separated, dried and concentrated under reduced pressure, leaving 9.6 g. of crude product which is used directly in the next step. ##STR15##

Workup

  1. additionAfter the addition
  2. stirringthe mixture is rapidly stirred for 15 min
  3. filtrationThe reaction is then filtered by suction through a pad of filter aid
  4. customThe organic layer is separated
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customleaving 9.6 g

Sources & evidence

ORD record
ord-ceda8a4d3d764a798064ec8dccea5e95
Source dataset
uspto-grants-1980_04
Patent number
US04199354

Linked notes

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