1,3-Dimethoxybenzene → 1,3-Dimethoxy-2-propylbenzene

HRID 864515Notes

Reaction equation

HRID 864515 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[CH:4]=1.[CH2:11]([Li])[CH2:12][CH2:13]C.C(I)CC>O1CCCC1.CCCCCC>[CH2:11]([C:4]1[C:3]([O:2][CH3:1])=[CH:8][CH:7]=[CH:6][C:5]=1[O:9][CH3:10])[CH2:12][CH3:13]

Participants

6

Reactant 3

HCID 90251,3-DimethoxybenzeneHCID 336431-IodopropaneHCID 178418339Butyllithium

Product 1

HCID 5248571,3-Dimethoxy-2-propylbenzeneYield 92%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

1,3-Dimethoxybenzene (20 g, 145 mmoles) in 200 ml of dry tetrahydrofuran was cooled to -10° C. To this solution at -10° C. was added n-butyllithium (100 ml of a 1.6 M solution in hexane, 160 mmoles) over 20 minutes. The reaction was then stirred for 2.5 hours at 0° C. At 0° C., propyl iodide (24.65 g, 145 mmoles) was added slowly over 15 minutes. When the addition was complete, the reaction was allowed to warm to room temperature and stirred overnight. After stirring overnight, the reaction was refluxed for 1.5 hours, then cooled to room temperature and quenched with ice. The tetrahydrofuran was removed under vacuum, and the resulting aqueous layer was extracted several times with diethyl ether. The organic extract was dried over magnesium sulfate and filtered to give a clear oil after solvent removal (26.11 g). The oil was purified by vacuum distillation to provide the title intermediate (24.0 g, 92%).

Workup

  1. additionWhen the addition
  2. temperatureto warm to room temperature
  3. stirringstirred overnight
  4. stirringAfter stirring overnight
  5. temperaturethe reaction was refluxed for 1.5 hours
  6. temperaturecooled to room temperature
  7. customquenched with ice
  8. customThe tetrahydrofuran was removed under vacuum
  9. extractionthe resulting aqueous layer was extracted several times with diethyl ether
  10. extractionThe organic extract
  11. dry with materialwas dried over magnesium sulfate
  12. filtrationfiltered
  13. customto give a clear oil
  14. customafter solvent removal (26.11 g)
  15. distillationThe oil was purified by vacuum distillation

Sources & evidence

ORD record
ord-1cb1000ac4c4461bbc51039f6a657e54
Source dataset
uspto-grants-1996_10
Patent number
US05563164

Reaction notes

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