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Nitric Acid → 3H-1,2-benzodioxole

HRID 1708174
Notes
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Reaction equation

HRID 1708174 reaction equation
C[C:2]1([C:11]2[CH:16]=[CH:15][C:14](C(F)(F)F)=[CH:13][CH:12]=2)OC2C=CC=CC=2[O:3]1.[N+]([O-])(O)=[O:22].O>ClC(Cl)C>[O:22]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH2:2][O:3]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 189611982-Methyl-2-[4-(trifluoromethyl)phenyl]-1,3-benzodioxole

Product 1

HCID 167221333H-1,2-benzodioxoleYield 82%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 2-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-benzodioxole (5.6 g) in dichloroethane (15 ml) was added over 10 minutes to vigorously stirred nitric acid (50% w/v, 25 ml) keeping the temperature at 15°-20° C. by means of a cooling bath. The resulting reaction mixture was stirred for a further 1 hour at 20° C., poured into water (200 ml) and extracted with methylene chloride (3×100 ml). After drying over anhydrous sodium sulphate, the extract was evaporated under reduced pressure. The residue was purified by chromatography on silica gel using methylene chloride as eluant, affording the pure product benzodioxole as a pale yellow oil (5.3 g, 82%).

Workup

  1. customat 15°-20° C.
  2. customThe resulting reaction mixture
  3. extractionextracted with methylene chloride (3×100 ml)
  4. dry with materialAfter drying over anhydrous sodium sulphate
  5. customthe extract was evaporated under reduced pressure
  6. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-7ddbf7d5a37a4876b2373b0bde4b66c9
Source dataset
uspto-grants-1994_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05356924

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes