Nitric Acid → 5-Nitro-2-(2,2,2-trifluoroethyl)-2-trifluoromethyl-1,3-benzodioxole

HRID 1081292Notes

Reaction equation

HRID 1081292 reaction equation
[F:1][C:2]([F:18])([F:17])[CH2:3][C:4]1([C:13]([F:16])([F:15])[F:14])[O:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[O:5]1.[N+:19]([O-])([OH:21])=[O:20].S(=O)(=O)(O)O>C(Cl)Cl>[N+:19]([C:11]1[CH:10]=[CH:9][C:7]2[O:8][C:4]([CH2:3][C:2]([F:1])([F:17])[F:18])([C:13]([F:15])([F:14])[F:16])[O:5][C:6]=2[CH:12]=1)([O-:21])=[O:20]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 536673032-(2,2,2-Trifluoroethyl)-2-(trifluoromethyl)-1,3-benzodioxole

Product 1

HCID 538772305-Nitro-2-(2,2,2-trifluoroethyl)-2-trifluoromethyl-1,3-benzodioxole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 54.4 g of 2-(2,2,2-trifluoroethyl)-2-trifluoromethyl-1,3-benzodioxole in 75 ml of methylene chloride was added dropwise at 10° C. to a mixture of 40 ml of 65% strength by weight nitric acid and 40 ml of concentrated sulphuric acid. The mixture was stirred for a further 1 hour at room texture and then poured into ice-water, the organic phase was separated off and the aqueous phase was extracted with methylene chloride. The combined organic phases were washed with water, dried, and freed from readily volatile constituents. There remained 95 g of the product (=86% of theory) with a melting point of 87° to 88° C.

Workup

  1. customthe organic phase was separated off
  2. extractionthe aqueous phase was extracted with methylene chloride
  3. washThe combined organic phases were washed with water
  4. customdried

Sources & evidence

ORD record
ord-e14b7bb38e24465fa1eec19ec522342f
Source dataset
uspto-grants-1996_12
Patent number
US05585395

Reaction notes

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