Nitric Acid → 7-Nitro-2,3-dihydro-1,4-benzodioxine-5-carboxylic acid

HRID 1413158Notes

Reaction equation

HRID 1413158 reaction equation
C(OC(=O)C)(=O)C.[O:8]1[C:13]2[CH:14]=[CH:15][CH:16]=[C:17]([C:18]([OH:20])=[O:19])[C:12]=2[O:11][CH2:10][CH2:9]1.[N+:21]([O-])([OH:23])=[O:22]>C(O)(=O)C>[N+:21]([C:15]1[CH:16]=[C:17]([C:18]([OH:20])=[O:19])[C:12]2[O:11][CH2:10][CH2:9][O:8][C:13]=2[CH:14]=1)([O-:23])=[O:22]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 781842,3-Dihydro-1,4-benzodioxin-5-carboxylic acid

Product 1

HCID 124645337-Nitro-2,3-dihydro-1,4-benzodioxine-5-carboxylic acidYield 27%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

160 ml of acetic acid, 160 ml of acetic anhydride and 100 g of 1,4-benzodioxane-5-carboxylic acid were introduced into a balloon flask provided with an agitator and a thermometer. The mixture was heated and a solution of 40 ml of nitric acid in 40 ml of acetic acid was added. The mixture was agitated at 40°-45° C. and then cooled. The crystals were dried off, washed and dried. 34 g of 7-nitro-1,4-benzodioxane-5-carboxylic acid were obtained (M.P.: 246° C.; yield: 27%).

Workup

  1. customprovided with an agitator
  2. temperatureThe mixture was heated
  3. temperaturecooled
  4. customThe crystals were dried off
  5. washwashed
  6. customdried

Sources & evidence

ORD record
ord-da5d0ed002d34ea1b2dd71950aca633c
Source dataset
uspto-grants-1981_02
Patent number
US04248885

Reaction notes

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