Epichlorohydrin → HCID 19808162, compound

HRID 1681052Notes

Reaction equation

HRID 1681052 reaction equation
[CH3:1][O:2][C:3](=[O:9])[C:4]([CH3:8])([CH3:7])[CH2:5][OH:6].[OH-].[Na+].C([CH:14]1[O:16][CH2:15]1)Cl.C[Si](O[Si](C)(C)C)(C)C>O>[CH2:1]([O:2][C:3](=[O:9])[C:4]([CH3:8])([CH3:7])[CH2:5][OH:6])[CH:15]1[O:16][CH2:14]1

Participants

6

Reactant 4

HCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 24764HexamethyldisiloxaneHCID 84152Methyl 3-hydroxypivalate

Product 1

HCID 19808162HCID 19808162, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

132 parts by wt. (1 mole) hydroxypivalic methyl ester, 48 parts by wt. (1.2 mole) sodium hydroxide solution and 250 ml water were heated for 1 hour at 100° C. in a 0.5-liter three-neck flask equipped with stirrer, thermometer and reflux cooler. The temperature was reduced to 50° C. To the mixture were added 276 parts by wt. (3 mole) epichlorohydrin (ECH) and 50 parts by wt. Dowex (Fluka AG, 1×8). The water was removed azeotropically at a temperature of 50° C. and at reduced pressure (200 mbar), the ECH being supplied back to the reaction mixture. The total reaction time was 3 hours. The salt formed was filtered off and washed twice with 20 ml ECH The excess ECH was removed by means of rotary film evaporation. Thus 167 parts by wt. hydroxypivalic glycidyl ester were obtained in the form of a light yellow liquid with an epoxide content of 5.5 meq/g and a hydroxy content of 307 mg KOH/g.

Workup

  1. customequipped with stirrer
  2. temperaturethermometer and reflux cooler
  3. customwas reduced to 50° C
  4. customThe water was removed azeotropically at a temperature of 50° C. and at reduced pressure (200 mbar)
  5. customThe salt formed
  6. filtrationwas filtered off
  7. washwashed twice with 20 ml ECH The excess ECH
  8. customwas removed by means of rotary film evaporation

Sources & evidence

ORD record
ord-02b7947e155144e8aed514aeb457f45d
Source dataset
uspto-grants-1992_12
Patent number
US05168110

Reaction notes

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