Ethylene Glycol → 2-(8-Bromooctyl)-1,3-dioxolane

HRID 1472734Notes

Reaction equation

HRID 1472734 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[O:11].[CH2:12](O)[CH2:13][OH:14].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]1[O:14][CH2:13][CH2:12][O:11]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 5433309-Bromononanal

Product 1

HCID 118323182-(8-Bromooctyl)-1,3-dioxolaneYield 79.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

9-Bromononanal (28.0 g, assumed 120 mmol), ethylene glycol (33.6 mL, 600 mmol) and para-toluenesulphonic acid (2.7 g, 13 mmol) in toluene (210 mL) were heated at reflux for 20 hours. The reaction was cooled to RT and quenched with saturated aqueous sodium bicarbonate solution (300 mL). The resultant mixture was extracted with diethyl ether (×2). The combined organic extracts were washed with saturated aqueous sodium bicarbonate solution, water and brine (100 mL). The organic phase was dried (magnesium sulphate), filtered and evaporated under reduced pressure to afford the title compound (25.2 g, 79%).

Workup

  1. temperatureat reflux for 20 hours
  2. customquenched with saturated aqueous sodium bicarbonate solution (300 mL)
  3. extractionThe resultant mixture was extracted with diethyl ether (×2)
  4. washThe combined organic extracts were washed with saturated aqueous sodium bicarbonate solution, water and brine (100 mL)
  5. dry with materialThe organic phase was dried (magnesium sulphate)
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-6c12bedaa7ff49e2bd104dcd5f8cd81f
Source dataset
uspto-grants-2015_04
Patent number
US09012644B2

Reaction notes

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