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Nitric Acid → 2,4-Diisopropyl-1-nitrobenzene

HRID 586676
Notes
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Reaction equation

HRID 586676 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH:5]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH:14]([CH3:16])[CH3:15])[CH:9]=1)([CH3:7])[CH3:6]>C(O)(=O)C.C(OC(=O)C)(=O)C.O.CCCCCC>[CH:5]([C:8]1[CH:9]=[C:10]([CH:14]([CH3:16])[CH3:15])[CH:11]=[CH:12][C:13]=1[N+:1]([O-:4])=[O:2])([CH3:7])[CH3:6]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 2

HCID 944Nitric AcidHCID 74501,3-Diisopropylbenzene

Product 1

HCID 223357262,4-Diisopropyl-1-nitrobenzeneYield 98%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 7918Acetic Anhydride
Solvent
HCID 8058HexaneSolvent

Procedure

Nitric acid (70%) (15.6 g, 185 mmol) was added slowly to a solution of 1,3-di-iso-propyl-benzene (available from Aldrich) (20 g, 123 mmol) in acetic acid (50 mL) and acetic anhydride (50 mL) at 0° C. over 20 min. After stirring at room temperature for 1 hour, the reaction mixture was diluted with water (250 mL) and hexane (500 mL). The organic layer was then washed with with water (50 mL), saturated Na2CO3 (50 mL), dried (Na2SO4) and concentrated to give the title compound in a crude form (25 g, 98% yield) as a colorless oil:

Workup

  1. washThe organic layer was then washed with with water (50 mL), saturated Na2CO3 (50 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e4a5090f80d14d719bf6c304ea57d41b
Source dataset
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06936636B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes