Guaiacol → 2,3-Epoxypropyl 4'-methoxyphenyl ether

HRID 1838802Notes

Reaction equation

HRID 1838802 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1O.[CH2:10]([CH:12]1[O:14][CH2:13]1)Cl.C([O-])([O-])=[O:16].[K+].[K+]>CC(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:16][CH2:10][CH:12]2[O:14][CH2:13]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 460GuaiacolHCID 7835EpichlorohydrinHCID 11430Potassium Carbonate

Product 1

HCID 166462,3-Epoxypropyl 4'-methoxyphenyl ether

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
70 °C

Procedure

2-methoxyphenol (1.0 g, 8.0 mmol) and epichlorohydrin (3.7 g, 40.0 mmol) were dissolved in acetone (20 mL). K2CO3 (2.2 g, 16.0 mmol) was added and the mixture was heated at 70° C. for 24 h. The reaction mixture was concentrated in vacuo. The residue was dissolved 100 mL of EtOAc, washed with 100 mL water, dried over MgSO4 and filtered. The mixture was evaporated to dryness and the residue was purified using column chromatography (2:1, hexane:ethyl acetate) to afford compound 6.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved 100 mL of EtOAc
  3. washwashed with 100 mL water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customThe mixture was evaporated to dryness
  7. customthe residue was purified

Sources & evidence

ORD record
ord-20009ae888a04f47928a578ec1a1f14f
Source dataset
uspto-grants-2004_01
Patent number
US06677336B2

Reaction notes

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