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Dimethylformamide → 4-Butoxy-1-methyl-2-nitrobenzene

HRID 72196
Notes
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Reaction equation

HRID 72196 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH2:12](Br)[CH2:13][CH2:14][CH3:15].C(=O)([O-])[O-].[Na+].[Na+].CN(C=O)C>CC(OC)(C)C>[CH2:12]([O:8][C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1)[CH2:13][CH2:14][CH3:15]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8002Butyl bromideHCID 10340Sodium CarbonateHCID 162713-Nitro-p-cresol

Product 1

HCID 689772014-Butoxy-1-methyl-2-nitrobenzene

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-methyl-3-nitrophenol (10.0 g), butyl bromide (9.4 g), sodium carbonate (6.9 g) and DMF (50 mL) was heated at 80° C. for 7 hours. The cooled reaction solution was diluted with MTBE and washed twice each with water and sodium hydroxide solution. The organic phase was dried and concentrated. The product with the molecular weight of 209.25 (C11H15NO3) was obtained in this way; MS (ESI): 210 (M+H+).

Workup

  1. customThe cooled reaction solution
  2. washwashed twice each with water and sodium hydroxide solution
  3. customThe organic phase was dried
  4. concentrationconcentrated
  5. customThe product with the molecular weight of 209.25 (C11H15NO3) was obtained in this way

Sources & evidence

ORD record
ord-b54f415575cc437c907cf99427af312b
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08828991B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes