Nitric Acid → HCID 18330872, compound

HRID 2271265Notes

Reaction equation

HRID 2271265 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Cl:5][C:6]1[C:11]([Cl:12])=[CH:10][CH:9]=[CH:8][C:7]=1[C:13]([Cl:16])([Cl:15])[Cl:14].S(=O)(=O)(O)O>>[Cl:5][C:6]1[C:11]([Cl:12])=[CH:10][C:9]([N+:1]([O-:4])=[O:2])=[CH:8][C:7]=1[C:13]([Cl:16])([Cl:14])[Cl:15]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 1693771,2-Dichloro-3-(trichloromethyl)benzene

Product 1

HCID 18330872HCID 18330872, compoundYield 58.2%

Conditions

Temperature
25 °C

Procedure

62 g of fuming nitric acid were added dropwise to 100 g of 2,3-dichlorobenzotrichloride at −10 to +10° C. in the course of 10 minutes, followed by 62 g of 96% by weight sulphuric acid. The reaction mixture was initially stirred at 20 to 30° C. for 2 hours, then cooled down, discharged onto ice and extracted 3× with 100 ml of dichloromethane each time. The combined organic phases were washed with 100 ml of water, 3×100 ml of saturated aqueous sodium bicarbonate solution and 100 ml of aqueous sodium chloride solution, dried over magnesium sulphate and evaporated. The crude product (99 g, purity 100%, 84.4% of theory) was recrystallized from ethanol to obtain 68 g (=58.2% of theory) of 2,3-dichloro-5-nitro-benzotrichloride (mp. 97 to 99° C.), while the other isomers ended up in the residue.

Workup

  1. temperaturecooled down
  2. extractionextracted 3× with 100 ml of dichloromethane each time
  3. washThe combined organic phases were washed with 100 ml of water, 3×100 ml of saturated aqueous sodium bicarbonate solution and 100 ml of aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customThe crude product (99 g, purity 100%, 84.4% of theory) was recrystallized from ethanol

Sources & evidence

ORD record
ord-2152898c2b3640219ceb64a762f92e83
Source dataset
uspto-grants-2001_12
Patent number
US06333434B1

Reaction notes

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