Ethylene Glycol → 2,2-Dibutyl-1,3,2-dioxastannolane

HRID 1265229Notes

Reaction equation

HRID 1265229 reaction equation
[CH2:1]([Sn:5](=[O:10])[CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2][CH2:3][CH3:4].[CH2:11](O)[CH2:12][OH:13]>C1C=CC=CC=1>[CH2:1]([Sn:5]1([CH2:6][CH2:7][CH2:8][CH3:9])[O:13][CH2:12][CH2:11][O:10]1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 174Ethylene GlycolHCID 61221Dibutyltin oxide

Product 1

HCID 166839432,2-Dibutyl-1,3,2-dioxastannolaneYield 94.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

24.98 g (0.1 mol) of dibutyltin oxide and 6.21 g (0.1 mol) of ethylene glycol were introduced into a 500 ml reaction vessel equipped with a Dean-Stark device, and the atmosphere in the reaction vessel was replaced by argon. 250 ml of benzene was added, and the mixture was dehydrated by azeotropic distillation at 93° C. and stirred for 4 hours during which it became an uniform solution. Then, the solution was filtered while it was hot. The benzene was distilled off under reduced pressure, and the resulting white solids were dried at 60° C. for 3 hours in vaccuo to give 1,1-dibutylstanna-2,5-dioxacyclopentane, 27.6 g (94.2% yield).

Workup

  1. customequipped with a Dean-Stark device
  2. distillationthe mixture was dehydrated by azeotropic distillation at 93° C.
  3. filtrationThen, the solution was filtered while it
  4. distillationThe benzene was distilled off under reduced pressure
  5. customthe resulting white solids were dried at 60° C. for 3 hours in vaccuo

Sources & evidence

ORD record
ord-18dd816d8fed49c387b95e74ab9f11b5
Source dataset
uspto-grants-2003_04
Patent number
US06545112B2

Reaction notes

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