Eugenol → 4-Propylguaiacol

HRID 2300697Notes

Reaction equation

HRID 2300697 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].C1(C)C=CC(S(NN)(=O)=O)=CC=1.CC([O-])=O.[Na+]>C(COC)OC.O>[CH3:12][O:11][C:6]1[CH:5]=[C:4]([CH2:1][CH2:2][CH3:3])[CH:9]=[CH:8][C:7]=1[OH:10]

Participants

6

Reactant 3

HCID 3314EugenolHCID 15303P-ToluenesulfonylhydrazideHCID 517045Sodium Acetate

Product 1

HCID 177394-PropylguaiacolYield 48.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 123 mg (0.75 mmole) of 4-allyl-2-methoxyphenol (eugenol) and 1.4 gm (7.5 mmole)of p-toluenesulfonhydrazide in 15 ml of dimethoxyethane under reflux was added a solution of 1.7 gm of NaOAc in 15 ml water over a 4 hour period. The mixture was cooled to room temperature, poured into 20 ml of water, and extracted three times with 30 ml of CH2Cl2. The combined organic layers were washed with 50 ml of water, dried over MgSO4, and concentrated under vacuo. The resulting solid was flash chromatographed over silica gel using 10% ethyl acetate in hexane to afford 60 mg of 2-methoxy-4-propylphenol in 48% yield.

Workup

  1. extractionextracted three times with 30 ml of CH2Cl2
  2. washThe combined organic layers were washed with 50 ml of water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under vacuo
  5. customchromatographed over silica gel using 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-55c82a1c9f354f10a39f29ad7b1d99d6
Source dataset
uspto-grants-2002_12
Patent number
US06498191B2

Reaction notes

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