Peracetic Acid → 4-(2,3-Epoxypropyl)-2,6-diphenylphenyl glycidyl ether

HRID 4149Notes

Reaction equation

HRID 4149 reaction equation
[CH2:1]([O:5][C:6]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:10][C:9]([CH2:18][CH:19]=[CH2:20])=[CH:8][C:7]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH:2]1[O:4][CH2:3]1.C(OO)(=[O:29])C>C1(C)C=CC=CC=1.C([O-])(=O)C.[Na+]>[CH2:1]([O:5][C:6]1[C:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:8][C:9]([CH2:18][CH:19]2[O:29][CH2:20]2)=[CH:10][C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH:2]1[O:4][CH2:3]1

Participants

5

Reactant 2

HCID 6585Peracetic AcidHCID 536917844-Allyl-2,6-diphenylphenyl glycidyl ether

Product 1

HCID 201527054-(2,3-Epoxypropyl)-2,6-diphenylphenyl glycidyl etherYield 86.9%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 517045Sodium AcetateSolvent

Procedure

A 100 ml sulfurating flask equipped with stirrer, cooler, thermometer and drip funnel is charged with 13.7 g (0.04 mole) of 4-allyl-2,6-diphenylphenyl glycidyl ether in 20 ml of toluene and 0.7 g of sodium acetate. Over 2 hours, 9.13 g (0.048 mole) of 40% peracetic acid are added at a temperature in the range from 30° to 50° C. When the dropwise addition is complete, the reaction mixture is stirred for a further 7 hours. When the reaction is complete, the reaction mixture is diluted with 700 ml of toluene, the resultant aqueous phase is separated and the organic phase is washed with two 150 ml portions of NaHCO3 (5%) and then washed with 150 ml of water. The organic phase is dried over Na2SO4 and made peroxide-free with Na2SO3 and filtered. The filtrate is concentrated, affording 12.46 g (86.5%) of a yellow resin with an epoxide content of 4.99 eq/kg (89.5%) and a viscosity of 6850 mPas/40° C.

Workup

  1. customequipped with stirrer
  2. additionWhen the dropwise addition
  3. customthe resultant aqueous phase is separated
  4. washthe organic phase is washed with two 150 ml portions of NaHCO3 (5%)
  5. washwashed with 150 ml of water
  6. dry with materialThe organic phase is dried over Na2SO4
  7. filtrationfiltered
  8. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-a11e6358c0444cb68a62cdc6256a2d8a
Source dataset
uspto-grants-1988_02
Patent number
US04724031

Reaction notes

Loading…