Nitric Acid → 8-Nitro-2,4-bis(trichloromethyl)-2H,4H-1,3-benzodioxine-6-carboxylic acid

HRID 224390Notes

Reaction equation

HRID 224390 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Cl:5][C:6]([Cl:25])([Cl:24])[CH:7]1[O:12][CH:11]([C:13]([Cl:16])([Cl:15])[Cl:14])[C:10]2[CH:17]=[C:18]([C:21]([OH:23])=[O:22])[CH:19]=[CH:20][C:9]=2[O:8]1>S(=O)(=O)(O)O>[N+:1]([C:20]1[C:9]2[O:8][CH:7]([C:6]([Cl:5])([Cl:24])[Cl:25])[O:12][CH:11]([C:13]([Cl:16])([Cl:14])[Cl:15])[C:10]=2[CH:17]=[C:18]([C:21]([OH:23])=[O:22])[CH:19]=1)([O-:4])=[O:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 1941342,4-Bis(trichloromethyl)-2H,4H-1,3-benzodioxine-6-carboxylic acid

Product 1

HCID 233329358-Nitro-2,4-bis(trichloromethyl)-2H,4H-1,3-benzodioxine-6-carboxylic acid

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Nitric acid (d=1.54, 10 ml.) was added to a stirred suspension of 2,4-bis(trichloromethyl)benzo[1,3]dioxin-6-carboxylic acid (5 g.) in concentrated sulphuric acid (25 ml.), and the resulting suspension was stirred at room temperature for 2 hrs. The reaction mixture was filtered, and the solid product was crystallised from a mixture of petroleum ether (b.p. 60°-80° C.) and ether to give 8-nitro-2,4-bis(trichloromethyl)benzo[1,3]dioxin-6-carboxylic acid, m.p. 211°-212° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solid product was crystallised from a mixture of petroleum ether (b.p. 60°-80° C.) and ether

Sources & evidence

ORD record
ord-adf387d90f00418189026259548a5f05
Source dataset
uspto-grants-1980_11
Patent number
US04232032

Reaction notes

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