Nitric Acid → 6-Nitro-2,3-dihydro-1,4-benzodioxine-5-carboxylic acid
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:16]1[CH:15]=[CH:14][C:13]2[O:8][CH2:9][CH2:10][O:11][C:12]=2[C:17]=1[C:18]([OH:20])=[O:19])([O-:23])=[O:22]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
1,600 ml of acetic acid, 1,600 ml of acetic anhydride, and 1000 g of 1,4-benzodioxane-5-carboxylic acid were introduced in a 6-liter balloon flask provided with an agitator and a thermometer. The mixture was heated to 40° C. and a solution of 400 ml of nitric acid in 400 ml of acetic acid was added. After the introduction, the mixture was stirred at 40°-45° C. for two hours and then cooled to 5° C. The precipitate was dried off, washed with 600 ml of acetic acid and then with water and dried at 40° C. 700 g of 7-nitro-1,4-benzodioxane-5-carboxylic acid were collected, the structure of which was confirmed by nuclear magnetic resonance (M.P.: 246° C.) The mother liquors were diluted with 25 liters of water and the obtained precipitate was dried off, washed with water and dried. 6-nitro-1,4-benzodioxane-5-carboxylic acid was obtained (M.P.: 188° C.).
Workup
- customprovided with an agitator
- temperaturecooled to 5° C
- customThe precipitate was dried off
- washwashed with 600 ml of acetic acid
- dry with materialwith water and dried at 40° C
- custom700 g of 7-nitro-1,4-benzodioxane-5-carboxylic acid were collected
- additionwere diluted with 25 liters of water
- customthe obtained precipitate was dried off
- washwashed with water
- customdried
Sources & evidence
- ORD record
- ord-2eaf11dd36b849af9e7225cfd14c5631
- Source dataset
- uspto-grants-1981_03
- Patent number
- US04255580
Reaction notes
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