Epichlorohydrin → HCID 53975804, compound

HRID 1514846Notes

Reaction equation

HRID 1514846 reaction equation
[C:1]([OH:11])(=[O:10])/[CH:2]=[CH:3]/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:12]([CH:14]1[O:16][CH2:15]1)Cl>[Br-].C([N+](CC)(CC)CC)C.O>[C:1]([O:11][CH2:12][CH:14]1[O:16][CH2:15]1)(=[O:10])[CH:2]=[CH:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 7835EpichlorohydrinHCID 444539Cinnamic Acid

Product 1

HCID 53975804HCID 53975804, compound

Reagents, catalysts & solvents 2

HCID 6285Tetraethylammonium BromideCatalystHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

To 7.5 g of trans-cinnamic acid (manufactured by Wako Pure Chemical) were added 3 g of tetraethylammonium bromide (manufactured by Wako Pure Chemical) and 100 ml of epichlorohydrin (manufactured by Wako Pure Chemical), the mixture was heated to reflux at 110° C. for 3 hours, 50 ml of distilled water was added thereto, an organic layer was separated, concentrated in vacuo at 80° C. and distilled under reduced pressure of 6 mmHg and the fraction of 130 to 160° C. was recovered to give 12 g of glycidyl cinnamate. An epoxy equivalent of this glycidyl cinnamate was 240.3.

Workup

  1. temperaturethe mixture was heated
  2. customan organic layer was separated
  3. concentrationconcentrated in vacuo at 80° C.
  4. distillationdistilled under reduced pressure of 6 mmHg
  5. customthe fraction of 130 to 160° C. was recovered

Sources & evidence

ORD record
ord-eebb9185c2de447c8ef1476e481019a7
Source dataset
uspto-grants-2012_07
Patent number
US08222399B2

Reaction notes

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