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Ethyl Acetate → 2-(2-Methyl-2-nitropropyl)naphthalene

HRID 895869
Notes
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Reaction equation

HRID 895869 reaction equation
Cl[CH:2]([C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=1)[C:3]([CH3:8])([N+:5]([O-:7])=[O:6])[CH3:4].C(OCC)(=O)C>CO.[C].[Pd]>[CH3:8][C:3]([N+:5]([O-:7])=[O:6])([CH3:4])[CH2:2][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 223824212-(1-Chloro-2-methyl-2-nitropropyl)naphthalene

Product 1

HCID 99646182-(2-Methyl-2-nitropropyl)naphthaleneYield 79.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

2-(1-Chloro-2-methyl-2-nitropropyl)naphthalene (200 mg) obtained in Step 4 was dissolved in methanol (5 ml) and ethyl acetate (5 ml) and to the solution was added 10% palladium carbon (20 mg). A hydrogenation reaction was performed at pressure of 3 atm for 2 hr. After filtration of the reaction mixture using Celite, the title compound (139 mg) was obtained by purification using silica gel column chromatography (n-hexane:ethyl acetate=95:5).

Workup

  1. customA hydrogenation reaction
  2. filtrationAfter filtration of the reaction mixture

Sources & evidence

ORD record
ord-5dcbc7852a8a4257bc5a54dfe953329b
Source dataset
uspto-grants-2005_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06916956B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes