Epichlorohydrin → HCID 20059095, compound

HRID 1085880Notes

Reaction equation

HRID 1085880 reaction equation
[CH3:1][O:2][CH:3]([O:11][CH3:12])[C:4]1[O:8][C:7]([CH2:9][OH:10])=[CH:6][CH:5]=1.[OH-].[Na+].[CH2:15]([CH:17]1[O:19][CH2:18]1)Cl>C(C(C)=O)C>[CH3:1][O:2][CH:3]([O:11][CH3:12])[C:4]1[O:8][C:7]([CH2:9][O:10][CH2:15][CH:17]2[O:19][CH2:18]2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 5881272-Furanmethanol, 5-(dimethoxymethyl)-

Product 1

HCID 20059095HCID 20059095, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

5-Glycidoxymethyl furfuraldehyde dimethyl acetal was prepared by adding a total of 6.0 g (0.035 mole) of 5-hydroxymethyl furfuraldehyde dimethyl acetal (HMFA) to 1.54 g sodium hydroxide (0.038 mole) in a 100 ml round bottom flask equipped with magnetic stir bar, reflux condenser, and nitrogen inlet. After stirring for 30 min., 3.89 g (0.042 mole) of epichlorohydrin in 50 ml. of methyl ethyl ketone was added quickly, and the reaction mixture was allowed to reflux overnight under an inert (nitrogen) atmosphere. The mixture was then cooled, filtered, and the solvent removed under vacuum. The resulting oil was mixed with 250 ml of toluene and the toluene was distilled off at atmospheric pressure to remove any residual epichlorohydrin. The sample was freed of toluene by subjecting it to high vacuum overnight.

Workup

  1. customequipped with magnetic stir bar
  2. temperaturereflux condenser, and nitrogen inlet
  3. temperatureto reflux overnight under an inert (nitrogen) atmosphere
  4. temperatureThe mixture was then cooled
  5. filtrationfiltered
  6. customthe solvent removed under vacuum
  7. additionThe resulting oil was mixed with 250 ml of toluene
  8. distillationthe toluene was distilled off at atmospheric pressure
  9. customto remove any residual epichlorohydrin
  10. customto high vacuum overnight

Sources & evidence

ORD record
ord-af85bb75662b4c52936da512d0c90518
Source dataset
uspto-grants-1991_04
Patent number
US05011918

Reaction notes

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