1-Bromo-3-methylbutane → 4-(3-Methylbutoxy)-2-nitrotoluene

HRID 1606109Notes

Reaction equation

HRID 1606109 reaction equation
[N+:1]([C:4]1[C:9]([CH3:10])=[CH:8][CH:7]=[C:6]([OH:11])[CH:5]=1)([O-:3])=[O:2].[CH2:12](Br)[CH2:13][CH:14]([CH3:16])[CH3:15].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:15][CH:14]([CH3:16])[CH2:13][CH2:12][O:11][C:6]1[CH:7]=[CH:8][C:9]([CH3:10])=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1

Participants

5

Reactant 3

HCID 78911-Bromo-3-methylbutaneHCID 11430Potassium CarbonateHCID 162713-Nitro-p-cresol

Product 1

HCID 215459694-(3-Methylbutoxy)-2-nitrotoluene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 50 parts of 3-nitro-p-cresol, 94 parts of isoamyl bromide and 94.2 parts of anhydrous potassium carbonate in 650 parts of acetone was stirred and heated under reflux for 18 hours. Insoluble material was filtered off and washed with acetone and the total acetone solution was evaporated. An oil remained which was partitioned between 250 parts of ether and 500 parts of water. The ethereal layer was isolated dried over anhydrous magnesium sulphate then evaporated to leave 66.6 parts of 4-(3-methylbutoxy)-2-nitrotoluene as a pale yellow oil.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 18 hours
  3. filtrationInsoluble material was filtered off
  4. washwashed with acetone
  5. customthe total acetone solution was evaporated
  6. customwas partitioned between 250 parts of ether and 500 parts of water
  7. customThe ethereal layer was isolated
  8. dry with materialdried over anhydrous magnesium sulphate
  9. customthen evaporated

Sources & evidence

ORD record
ord-fa653e091d1a4f149fbf1e25c83f77cf
Source dataset
uspto-grants-1976_04
Patent number
US03952013

Reaction notes

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