Nitric Acid → 6-Nitro-2,3-dihydro-1,4-benzodioxine-5-carboxylic acid

HRID 127442

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

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
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04255580

Linked notes

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