Ethanol → (1-Methyl-2,6,7-trioxabicyclo[2.2.2]octan-4-yl)methanol

HRID 379209Notes

Reaction equation

HRID 379209 reaction equation
[C:1]([O:9][CH2:10][CH3:11])([O:6][CH2:7]C)([O:3][CH2:4]C)[CH3:2].[OH:12][CH2:13]C(CO)(CO)CO.C(O)C>CC1C=CC(S(O)(=O)=O)=CC=1.COCCOCCOC>[CH2:13]([C:11]12[CH2:4][O:3][C:1]([CH3:2])([O:6][CH2:7]1)[O:9][CH2:10]2)[OH:12]

Participants

6

Reactant 3

HCID 702EthanolHCID 8285PentaerythritolHCID 66221Triethyl orthoacetate

Product 1

HCID 13547990(1-Methyl-2,6,7-trioxabicyclo[2.2.2]octan-4-yl)methanolYield 88.8%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 8150DiglymeSolvent2×

Conditions

Temperature
170 °C

Procedure

Into a flask equipped with a stirrer, a distilling column, a nitrogen inlet, a heating jacket, and a thermometer were charged 486 g of triethyl orthoacetate, 408 g of pentaerythritol, 300 g of diethylene glycol dimethyl ether, and 0.9 g of PTSA. The mixture was gradually heated to 170° C. over a period of 5 hours. During this time 490 g of distillate were obtained. The distillate contained mostly ethanol and small amounts of diethylene glycol dimethyl ether. The temperature was lowered to 100° C., and the remaining diethylene glycol dimethyl ether was distilled off under reduced pressure (30 mbar). The residue was subjected to vacuum distillation. The fraction having a boiling temperature of 126-130° C. at a pressure of 4 mbar yielded 426 g of oil. This oil solidified to a clear solid having a melting point of 99° C. and had the following structure

Workup

  1. customInto a flask equipped with a stirrer
  2. customDuring this time 490 g of distillate were obtained
  3. customwas lowered to 100° C.
  4. distillationthe remaining diethylene glycol dimethyl ether was distilled off under reduced pressure (30 mbar)
  5. distillationThe residue was subjected to vacuum distillation

Sources & evidence

ORD record
ord-6199c1988c404c0a9b6d85cbb575e22a
Source dataset
uspto-grants-2001_10
Patent number
US06297329B1

Reaction notes

Loading…