Eugenol → HCID 15176726, compound

HRID 1494159Notes

Reaction equation

HRID 1494159 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([O:11][CH3:12])[CH:5]=1)[CH:2]=[CH2:3].[OH-].[Na+].[CH2:15](Cl)[CH:16]=[CH2:17]>C(O)CC>[CH2:17]([C:8]1[CH:9]=[C:4]([CH2:1][CH:2]=[CH2:3])[CH:5]=[C:6]([O:11][CH3:12])[C:7]=1[OH:10])[CH:16]=[CH2:15]

Participants

5

Reactant 3

HCID 3314EugenolHCID 7850Allyl chlorideHCID 14798Sodium Hydroxide2×

Product 1

HCID 15176726HCID 15176726, compound

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Conditions

Temperature
70 °C

Procedure

To the solution of 162.4 g (1 mol) of 4-allyl-2-methoxyphenol (Eugenol) in 500 ml of 1-propanol heated to 70° C., 40 g (1 mol) of NaOH pellets are added and the mixture is stirred at 90° C. until NaOH is dissolved. The solution is cooled to 70° C. and 95.6 g (1.25 mol) of allyl chloride are added dropwise. After that, the reaction mixture is refluxed at 90° C. for 3 hours, then filtered, and propanol distilled off. 500 ml of toluene are added to the residue and the obtained solution is washed with 10% NaOH in water. The toluene-water mixture is distilled off and 6.5 g of LiCl and 1.6 g of Na2CO3 are added. The reaction mixture is heated to 130° C. under vacuum and kept at this temperature for 1 hour, then filtered and distilled under vacuum. The product 2,4-diallyl-6-methoxyphenol is off-white, low viscosity liquid (viscosity is 7 cPs at 25° C.) having a boiling point of 109°-112° C. (2-3 mm Hg), the structure is confirmed by IR and NMR Data. Yield is 163 g (80%).

Workup

  1. dissolutionis dissolved
  2. temperatureAfter that, the reaction mixture is refluxed at 90° C. for 3 hours
  3. filtrationfiltered
  4. distillationpropanol distilled off
  5. addition500 ml of toluene are added to the residue
  6. washthe obtained solution is washed with 10% NaOH in water
  7. distillationThe toluene-water mixture is distilled off
  8. addition6.5 g of LiCl and 1.6 g of Na2CO3 are added
  9. temperatureThe reaction mixture is heated to 130° C. under vacuum
  10. filtrationfiltered
  11. distillationdistilled under vacuum
  12. customlow viscosity liquid (viscosity is 7 cPs at 25° C.)

Sources & evidence

ORD record
ord-a40de0beab094d818792ddd34749b8f3
Source dataset
uspto-grants-1991_06
Patent number
US05025095

Reaction notes

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