Formic Acid → 4-(2,3-Epoxypropyl)-2,6-dimethylphenyl glycidyl ether

HRID 4147Notes

Reaction equation

HRID 4147 reaction equation
[CH2:1]([O:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([CH2:13][CH:14]=[CH2:15])=[CH:8][C:7]=1[CH3:16])[CH:2]1[O:4][CH2:3]1.C(O)=[O:18].OO>C(Cl)(Cl)Cl>[CH2:1]([O:5][C:6]1[C:7]([CH3:16])=[CH:8][C:9]([CH2:13][CH:14]2[O:18][CH2:15]2)=[CH:10][C:11]=1[CH3:12])[CH:2]1[O:4][CH2:3]1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 784Hydrogen PeroxideHCID 198362214-Allyl-2,6-dimethylphenyl glycidyl ether

Product 1

HCID 201527044-(2,3-Epoxypropyl)-2,6-dimethylphenyl glycidyl etherYield 85.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A 350 ml sulfurating flask equipped with thermometer, stirrer, cooler and drip funnel is charged with 21.8 g (0.10 mole) of 4-allyl-2,6-dimethylphenyl glycidyl ether, 10.9 g (0.24 mole) of formic acid and 135 ml of chloroform. At room temperature, 23.2 g (0.47 mole) of hydrogen peroxide are then added dropise over 4 hours. The reaction miture is held at this temperature overnight. It is subsequently taken up in chloroform and the resultant solution is washed twice with 3% NaOH solution until neutral, made peroxide-free with sodium sulfite, dried over sodium sulfate and filtered. The filtrate is concentrated, affording 20.03 g (80.50% of theory) of 4-(2,3-epoxypropyl)-2,6-dimethylphenyl glycidyl ether in the form of a low viscous resin; epoxide content 7.7 equivalents/kg (90.11% of theory).

Workup

  1. customequipped with thermometer, stirrer, cooler and drip funnel
  2. customis held at this temperature overnight
  3. washthe resultant solution is washed twice with 3% NaOH solution until neutral,
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-2a2a0d78cbcc499984b40bbe74b117a2
Source dataset
uspto-grants-1988_02
Patent number
US04724031

Reaction notes

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