Trimethylolpropane → 1-(1-Bromoethyl)-4-ethyl-2,6,7-trioxabicyclo[2.2.2]octane

HRID 2295527Notes

Reaction equation

HRID 2295527 reaction equation
[CH2:1]([O:3][C:4]([O:11][CH2:12][CH3:13])([O:8][CH2:9]C)[CH:5]([Br:7])[CH3:6])C.[CH2:14]([C:16](CO)(CO)CC)O>C1(C)C=CC(S(O)(=O)=O)=CC=1.C(O)C>[Br:7][CH:5]([C:4]12[O:3][CH2:1][C:13]([CH2:14][CH3:16])([CH2:9][O:8]1)[CH2:12][O:11]2)[CH3:6]

Participants

5

Reactant 2

HCID 6510TrimethylolpropaneHCID 27792852-Bromo-1,1,1-triethoxypropane

Product 1

HCID 204748331-(1-Bromoethyl)-4-ethyl-2,6,7-trioxabicyclo[2.2.2]octaneYield 63.7%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 702EthanolSolvent

Conditions

Temperature
140 °C

Procedure

25.5 g (0.1 moles) of the product obtained in step (a) above, 13.4 g (0.1 moles) of trimethylolpropane and 0.05 g of p-toluenesulfonic acid were placed in a flask fitted with a Dean & Stark condenser and the contents of the flask were heated at 140° C. for about 2 hours. The reaction was stopped when a theoretical amount of ethyl alcohol was evaporated off, after which the reaction solution was distilled under reduced pressure using a Vigreaux distillation column to yield 16 g (63%) of the desired product having a boiling point of 81°-83° C./0.1 mmHg.

Workup

  1. customfitted with a Dean & Stark condenser
  2. customwas evaporated off
  3. distillationafter which the reaction solution was distilled under reduced pressure
  4. distillationa Vigreaux distillation column

Sources & evidence

ORD record
ord-02791f7f5d8f4b5a8e0a50cffeb017c0
Source dataset
uspto-grants-1984_01
Patent number
US04425473

Reaction notes

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