Nitric Acid → HCID 14838332, compound

HRID 2379716Notes

Reaction equation

HRID 2379716 reaction equation
[N+:1]([O-])(O)=O.[Cl:5][C:6]1[C:11]2[CH2:12][C:13]([CH3:16])([CH3:15])[O:14][C:10]=2[C:9]([C:17]([OH:19])=[O:18])=[CH:8][CH:7]=1>S(=O)(=O)(O)O>[NH2:1][C:7]1[CH:8]=[C:9]([C:17]([OH:19])=[O:18])[C:10]2[O:14][C:13]([CH3:16])([CH3:15])[CH2:12][C:11]=2[C:6]=1[Cl:5]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 14838229HCID 14838229, compound

Product 1

HCID 14838332HCID 14838332, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
5 °C

Procedure

To a mixture of 40 ml of nitric acid and 40 ml of sulfuric acid cooled to 5° C. by means of an external ice bath were added 10 g of 4-chloro-2,2-dimethyl-2,3-dihydro-7-benzofurancarboxylic acid over a period of 28 minutes. After stirring at 5° C. for 10 minutes, the mixture was added to ice with stirring. The resulting solid was collected by filtration and washed with water. After air drying, the residue was crystallized twice from ethyl acetate/hexane to provide 3.5 g of the desired subtitle intermediate, m.p. 260°-262° C.

Workup

  1. additionthe mixture was added to ice
  2. stirringwith stirring
  3. filtrationThe resulting solid was collected by filtration
  4. washwashed with water
  5. customAfter air drying
  6. customthe residue was crystallized twice from ethyl acetate/hexane

Sources & evidence

ORD record
ord-aca45aab94584b888443f2a28c14ee0e
Source dataset
uspto-grants-1994_11
Patent number
US05364863

Reaction notes

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