Epichlorohydrin → [(2-Iodo-5-methoxyphenoxy)methyl]oxirane

HRID 1906506Notes

Reaction equation

HRID 1906506 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[OH:10].[H-].[Na+].[CH2:13]([CH:15]1[O:17][CH2:16]1)Cl>>[I:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[O:10][CH2:13][CH:15]1[CH2:16][O:17]1

Participants

4

Reactant 3

HCID 7835EpichlorohydrinHCID 24758Sodium hydrideHCID 114140152-Iodo-5-methoxyphenol

Product 1

HCID 20212121[(2-Iodo-5-methoxyphenoxy)methyl]oxiraneYield 93%

Conditions

Temperature
5 °C

Procedure

A 5.0 g (0.02 mole) sample of 2-iodo-5-methoxyphenol was added in portions to a suspension of 1.01 g (0.021 mole) of 50% sodium hydride (from which the oil had been removed by washing with hexane) in 40 ml of dry DMF. The resulting solution was cooled to 5° C. and 9.14 g (0.099 mole) of epichlorohydrin was added. The mixture was heated at 60° C. for 15 minutes. The mixture was cooled and filtered through diatomaceous earth. The solvent was evaporated in vacuo from the filtrate. The residue was taken up in ether, the ether washed with water and brine, dried (MgSO4) and the solvent evaporated in vacuo to give 5.72 g (93% yield) of [(2-iodo-5-methoxyphenoxy)methyl]oxirane as a brown oil.

Workup

  1. customhad been removed
  2. washby washing with hexane) in 40 ml of dry DMF
  3. temperatureThe mixture was heated at 60° C. for 15 minutes
  4. temperatureThe mixture was cooled
  5. filtrationfiltered through diatomaceous earth
  6. customThe solvent was evaporated in vacuo from the filtrate
  7. washthe ether washed with water and brine
  8. dry with materialdried (MgSO4)
  9. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-e4565a4d053b434192bae8bf23f3dfc2
Source dataset
uspto-grants-1987_03
Patent number
US04652584

Reaction notes

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