Water → HCID 18519341, compound

HRID 2299253Notes

Reaction equation

HRID 2299253 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:12])[CH:5]=[C:6]([CH3:11])[C:7]=1[N+:8]([O-:10])=[O:9].Br[CH2:14][CH2:15][CH2:16][CH3:17].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH2:14]([O:12][C:4]1[CH:3]=[C:2]([CH3:1])[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([CH3:11])[CH:5]=1)[CH2:15][CH2:16][CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 8002Butyl bromideHCID 11430Potassium CarbonateHCID 1384663,5-Dimethyl-4-nitrophenol

Product 1

HCID 18519341HCID 18519341, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Formation of compound (c): A mixture of 3,5-dimethyl-4-nitrophenol (b) (2 g, 12 mmol), bromobutane (1.6 mL, 15 mmol), K2CO3 (2.1 g, 15 mmol) in DMF (6 mL) was stirred at 60° C. for 6 hours. The reaction mixture was poured into 50 mL of H2O and extracted with ether (3×50 mL). The combined ether layer was washed with H2O and subsequently with brine, dried over Na2SO4, filtered and concentrated to give compound (c), 4-butoxy-2,6-dimethyl-nitrobenzene (2.6 g, 97% yield) as a dark brown oil. 1H-NMR in CDCl3.

Workup

  1. extractionextracted with ether (3×50 mL)
  2. washThe combined ether layer was washed with H2O and subsequently with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6dd8f3015cd742bfbf8ae656d159e146
Source dataset
uspto-grants-2002_12
Patent number
US06495681B1

Reaction notes

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