Ethanol → 4-(Bromomethyl)-2,6,7-trioxabicyclo[2.2.2]octane

HRID 371168Notes

Reaction equation

HRID 371168 reaction equation
[Br:1][CH:2]([C:4]([CH2:9][OH:10])([CH2:7][OH:8])[CH2:5][OH:6])O.[CH2:11](OC(OCC)OCC)C.C(O)C>>[Br:1][CH2:2][C:4]12[CH2:9][O:10][CH:11]([O:8][CH2:7]1)[O:6][CH2:5]2

Participants

4

Reactant 3

HCID 702EthanolHCID 31214Ethyl orthoformateHCID 14646171HCID 14646171, compound

Product 1

HCID 202744834-(Bromomethyl)-2,6,7-trioxabicyclo[2.2.2]octane

Procedure

Monobromopentaerythritol from A (10 g, 0.05 mole) and 9 ml triethylorthoformate (0.05 mole) are mixed in a sublimation apparatus equipped with a side arm. The mixture is heated to about 100° C. with magnetic stirring, and 1,5 equivalents of ethanol are allowed to distill out. Then about 100 ml dioctyl phthalate and a trace of anhydrous p-toluenesulfonic acid are added. Under vacuum the mixture is heated to about 140°-150° C. Periodically the collected crystals are removed from the cold finger. After about 3 hours no more compound sublimes. The yield of 4-bromoethyl-2,6,7-trioxabicyclo[2.2.2]octane is 6.5 g (60%).

Workup

  1. customequipped with a side arm
  2. distillationto distill out
  3. additionThen about 100 ml dioctyl phthalate and a trace of anhydrous p-toluenesulfonic acid are added
  4. temperatureUnder vacuum the mixture is heated to about 140°-150° C
  5. customPeriodically the collected crystals are removed from the cold finger

Sources & evidence

ORD record
ord-bc925283a14143e7ac73dc9309727e42
Source dataset
uspto-grants-1985_07
Patent number
US04529786

Reaction notes

Loading…