Nitric Acid → HCID 14838331, compound

HRID 864373Notes

Reaction equation

HRID 864373 reaction equation
[N+:1]([O-:4])(O)=[O:2].[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>[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][C:7]=1[N+:1]([O-:4])=[O:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 14838229HCID 14838229, compound

Product 1

HCID 14838331HCID 14838331, 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 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-f2674e5a047849f48fe4f989f2b8a517
Source dataset
uspto-grants-1996_10
Patent number
US05563148

Reaction notes

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