Trimethylolpropane → 2,6,7-Trioxabicyclo(2.2.2)octane, 4-ethyl-1-methyl-

HRID 1364975Notes

Reaction equation

HRID 1364975 reaction equation
[CH2:1]([C:3]([CH2:8][OH:9])([CH2:6][OH:7])[CH2:4][CH3:5])[OH:2].[C:10](OCC)(OCC)(OCC)[CH3:11].C1(C)C(S(O)(=O)=O)=CC=CC=1>>[CH2:4]([C:3]12[CH2:8][O:9][C:10]([CH3:11])([O:7][CH2:6]1)[O:2][CH2:1]2)[CH3:5]

Participants

4

Reactant 3

HCID 6510TrimethylolpropaneHCID 69252-Methylbenzenesulfonic acidHCID 66221Triethyl orthoacetate

Product 1

HCID 1652052,6,7-Trioxabicyclo(2.2.2)octane, 4-ethyl-1-methyl-

Procedure

Trimethylolpropane (268.0 g, 2.0 mol), triethyl orthoacetate (356.4 g, 2.20 mol) and toluene sulfonic acid (4.0 g) were charged into a oven dried round bottom flask equipped with a stirring bar, distillation head and under nitrogen. The resulting solution was heated until the theoretical amount od ethanol was collected. The reaction was cooled to room temperature. Fractional vacuum distillation afforded the product as a water clear liquid, boiling point 62.8-71.2° C. at 0.78-1.80 torr. Yield: 276.0 g (87.3%)

Workup

  1. customdried round bottom flask
  2. customequipped with a stirring bar
  3. distillationdistillation head
  4. temperatureThe resulting solution was heated until the theoretical amount od ethanol
  5. customwas collected
  6. distillationFractional vacuum distillation
  7. customafforded the product as a water clear liquid, boiling point 62.8-71.2° C. at 0.78-1.80 torr

Sources & evidence

ORD record
ord-affc0aa3faf54018902545206ae53976
Source dataset
uspto-grants-2011_02
Patent number
US07888440B2

Reaction notes

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