Nitrogen → 2-Methoxy-4-(prop-2-en-1-yl)-1-[(prop-2-en-1-yl)oxy]benzene

HRID 1087235Notes

Reaction equation

HRID 1087235 reaction equation
[C:1]1([O:11][CH3:12])[C:2](=[CH:4][CH:5]=[C:6]([CH:10]=1)[CH2:7][CH:8]=[CH2:9])[OH:3].N#N.[OH-].[Na+].[CH2:17](Cl)[CH:18]=[CH2:19]>O.CC(O)C>[CH3:12][O:11][C:1]1[CH:10]=[C:6]([CH2:7][CH:8]=[CH2:9])[CH:5]=[CH:4][C:2]=1[O:3][CH2:19][CH:18]=[CH2:17]

Participants

7

Reactant 4

HCID 947NitrogenHCID 3314EugenolHCID 7850Allyl chlorideHCID 14798Sodium Hydroxide

Product 1

HCID 217110342-Methoxy-4-(prop-2-en-1-yl)-1-[(prop-2-en-1-yl)oxy]benzeneYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

A multi-necked round bottom flask equipped with mechanical stirrer, thermometer, reflux condenser and dropping funnel was charged with 150 g of eugenol, 400 ml of 2-propanol and a gentle flow of N2 was introduced. A 40% NaOH solution (43.9 g NaOH, 1.1 mole in 66 g H2O) was added slowly to the externally cooled reaction vessel at a rate to maintain the internal temperature below 35° C. The mixture was stirred for 10 minutes and 113 ml (1.38 mole) of allyl chloride was added to the flask and heated to maintain a gentle reflux for 1 hour, at which time the reaction was complete (GC analysis). The flask was charged with 300 ml water. A Dean-Stark Trap and steam bath were used to azeotropically remove the 2-propanol. The distillation ceased when the temperature reached 94° C. and after cooling, 300 ml of hexane was added and the water layer separated. The organic layer was washed with water until the pH of the water wash was neutral, the layer was then dried over MgSO4, filtered and the solvent removed under vacuum. The product was vacuum distilled to yield 155 g (84%) of a pale yellow 3-[2-methoxy-4-(2-propenyl)phenoxy]propene.

Workup

  1. customA multi-necked round bottom flask equipped with mechanical stirrer
  2. temperaturethermometer, reflux condenser
  3. temperatureto maintain the internal temperature below 35° C
  4. temperatureheated
  5. temperatureto maintain
  6. temperaturea gentle reflux for 1 hour, at which time the reaction
  7. customto azeotropically remove the 2-propanol
  8. distillationThe distillation
  9. customreached 94° C.
  10. temperatureafter cooling
  11. addition300 ml of hexane was added
  12. customthe water layer separated
  13. washThe organic layer was washed with water until the pH of the water
  14. washwash
  15. dry with materialthe layer was then dried over MgSO4
  16. filtrationfiltered
  17. customthe solvent removed under vacuum
  18. distillationdistilled

Sources & evidence

ORD record
ord-a971d7476d9d477396e6e02641e66d69
Source dataset
uspto-grants-1991_07
Patent number
US05034473

Reaction notes

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