Allyl glycidyl ether → Diglycidyl ether

HRID 1278019Notes

Reaction equation

HRID 1278019 reaction equation
[CH2:1]([O:5][CH2:6][CH:7]=[CH2:8])[CH:2]1[O:4][CH2:3]1.ClC1C=C(C=CC=1)C(OO)=[O:14]>C(Cl)Cl>[O:5]([CH2:6][CH:7]1[CH2:8][O:14]1)[CH2:1][CH:2]1[CH2:3][O:4]1

Participants

4

Reactant 2

HCID 7838Allyl glycidyl etherHCID 70297m-Chloroperbenzoic acid

Product 1

HCID 16704Diglycidyl etherYield 156.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

28.54 g of allyl glycidyl ether (0.15 mole) (Aldrich) is dissolved in 1000 ml of methylene chloride and cooled to 0° in an ice bath. In one single addition 51.75 g of m-chloroperoxybenzoic acid (1.05 equiv. @ 85% tech) (Aldrich) is added and the reaction stirred rapidly at 0° for 4 hours. The reaction is allowed to slowly warm to room temperature and stirred overnight. The precipitated m-chlorobenzoic acid is removed via filtration and washed with 50 ml of cold CH2Cl2. The CH2Cl2 solution is then washed with 2×200 ml of saturated potassium carbonate solution and dried over Na2SO4. The CH2Cl2 is removed in vacuo yielding 30.6 g (94%) of 2,2'-(oxybismethylene)bisoxirane as a colorless liquid.

Workup

  1. temperaturecooled to 0° in an ice bath
  2. additionis added
  3. stirringstirred overnight
  4. customThe precipitated m-chlorobenzoic acid is removed via filtration
  5. washwashed with 50 ml of cold CH2Cl2
  6. washThe CH2Cl2 solution is then washed with 2×200 ml of saturated potassium carbonate solution
  7. dry with materialdried over Na2SO4
  8. customThe CH2Cl2 is removed in vacuo

Sources & evidence

ORD record
ord-10a07f84f0574ec9a49328a1e82497fc
Source dataset
uspto-grants-1981_07
Patent number
US04279902

Reaction notes

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