p-Toluenesulfonic acid → 2,6,7-Trioxabicyclo[2.2.2]octane, 1,4-diethyl-

HRID 379210Notes

Reaction equation

HRID 379210 reaction equation
[C:1]([O:10][CH2:11][CH3:12])([O:7][CH2:8]C)([O:4][CH2:5]C)[CH2:2][CH3:3].[CH2:13]([C:15](CO)(CO)CC)O.COCCOCCOC.CC1C=CC(S(O)(=O)=O)=CC=1>C(O)C>[CH2:2]([C:1]12[O:4][CH2:5][C:12]([CH2:13][CH3:15])([CH2:8][O:7]1)[CH2:11][O:10]2)[CH3:3]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 6510TrimethylolpropaneHCID 8150DiglymeHCID 66995Ethyl orthopropionate

Product 1

HCID 778432,6,7-Trioxabicyclo[2.2.2]octane, 1,4-diethyl-

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Into a flask as specified in Example 1 were charged 529 g of triethyl orthopropionate, 402 g of trimethylol propane, 330 g of diethylene glycol dimethyl ether, and 0.9 g of PTSA. The mixture was heated for 0.5 hour at 140° C., with 402 g of ethanol being distilled off. The temperature was lowered to 100° C., and the remaining diethylene glycol dimethyl ether was distilled off under reduced pressure. The residue was subjected to vacuum distillation. The fraction having a boiling temperature of 54° C. at a pressure of 0.5 mbar yielded 370 g of clear, low-viscous liquid having a boiling point of 223° C. at atmospheric pressure and with the following structure

Workup

  1. customInto a flask as specified in Example 1
  2. distillationdistilled off
  3. customwas lowered to 100° C.
  4. distillationthe remaining diethylene glycol dimethyl ether was distilled off under reduced pressure
  5. distillationThe residue was subjected to vacuum distillation
  6. customyielded 370 g of clear, low-viscous liquid

Sources & evidence

ORD record
ord-fee2c1939b754f3aa0d880dbf10e2afc
Source dataset
uspto-grants-2001_10
Patent number
US06297329B1

Reaction notes

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