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Cumene → 2-Nitropropan-2-ylbenzene

HRID 1885071
Notes
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Reaction equation

HRID 1885071 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[N:10]([O:12]C(C)(C)C)=[O:11].ON1C(=O)C2=CC=CC=C2C1=O.C(C1C=CC=CC=1)(C)=C.OC(C1C=CC=CC=1)(C)C>C(O)(=O)C>[CH3:2][C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)([N+:10]([O-:12])=[O:11])[CH3:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 7406CumeneHCID 7407Alpha-MethylstyreneHCID 10665N-HydroxyphthalimideHCID 10906Tert-Butyl nitriteHCID 120532-Phenyl-2-propanol

Product 1

HCID 36057092-Nitropropan-2-ylbenzene

Reagents, catalysts & solvents 1

HCID 176
Acetic Acid
Solvent

Conditions

Temperature
80 °C

Procedure

Isopropylbenzene (1 ml), t-butyl nitrite (1 mmol), N-hydroxyphthalimide (0.2 mmol), and acetic acid (1 ml) were placed in a flask and were stirred at 80° C. in an atmosphere of argon gas (1 atm=0.101 MPa) for 20 hours. The resulting reaction mixture was analyzed to find that isopropenylbenzene, (1-hydroxy-1-methylethyl)benzene, and (1-methyl-1-nitroethyl)benzene were formed in yields of 60%, 6%, and 7%, respectively.

Workup

  1. customThe resulting reaction mixture

Sources & evidence

ORD record
ord-43711ed7d8774679a6e128354179873a
Source dataset
uspto-grants-2004_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06768023B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes