Epichlorohydrin → HCID 15965804, compound

HRID 1792167Notes

Reaction equation

HRID 1792167 reaction equation
[OH:1][C:2]([CH3:7])([CH3:6])[C:3]([O-:5])=[O:4].[Na+].[CH2:9]([CH:11]1[O:13][CH2:12]1)Cl>[Cl-].C[N+](C)(C)C.O>[OH:1][C:2]([CH3:7])([CH3:6])[C:3]([O:5][CH2:9][CH:11]1[O:13][CH2:12]1)=[O:4]

Participants

5

Reactant 2

HCID 7835EpichlorohydrinHCID 23667177HCID 23667177, compound

Product 1

HCID 15965804HCID 15965804, compound

Reagents, catalysts & solvents 2

HCID 6379Tetramethylammonium chlorideCatalystHCID 962WaterSolvent2×

Conditions

Temperature
120 °C

Procedure

Into a 200 mL three-necked flask equipped with a stirrer and reflux tube was charged 37.83 g (0.3 mol) of sodium 2-hydroxyisobutyrate, 138.7 g (1.5 mol) of epichlorohydrin, 0.25 g of tetramethylammonium chloride and pure water at room temperature under normal pressure, and heated at temperatures from room temperature to an inner temperature of 120° C. over a period of 10 minutes, then, reacted while keeping this temperature for 1.5 hours, then, cooled to room temperature. To this was added water and allowed to stand for 1.5 hours, then, an organic solvent phase was removed. After epichlorohydrin was distilled off in a distillation apparatus equipped with a Vigreux distilling column, the obtained residual liquid was distilled under reduced pressure to obtain glycidyl 2-hydroxyisobutyrate. The charging molar ratio, reaction conditions and reaction yield, and the amount of by-products after distillation under reduced pressure are shown in Tables 1 and 2. The addition ratio of catalysts and water in the tables were calculated based on the total weight of a raw material compound of the formula (1), epichlorohydrin, catalyst and water.

Workup

  1. customInto a 200 mL three-necked flask equipped with a stirrer
  2. temperaturereflux tube
  3. customreacted
  4. customfor 1.5 hours
  5. temperaturecooled to room temperature
  6. customan organic solvent phase was removed
  7. distillationAfter epichlorohydrin was distilled off in a distillation apparatus
  8. customequipped with a Vigreux
  9. distillationdistilling column
  10. distillationthe obtained residual liquid was distilled under reduced pressure

Sources & evidence

ORD record
ord-4cfd76072bfd4a1c94c3b2d643eab6cf
Source dataset
uspto-grants-2006_07
Patent number
US07074946B2

Reaction notes

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