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

HRID 332636

Reaction equation

HRID 332636 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 resulting mixture was extracted with diethyl ether (2×500 mL). The combined organic extracts were washed with saturated aqueous sodium bicarbonate solution (300 mL), water (300 mL), brine (100 mL), dried (magnesium sulfate), 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 resulting mixture was extracted with diethyl ether (2×500 mL)
  4. washThe combined organic extracts were washed with saturated aqueous sodium bicarbonate solution (300 mL), water (300 mL), brine (100 mL)
  5. dry with materialdried (magnesium sulfate)
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-a4c714a186604d398b6b4ba90372980c
Source dataset
uspto-grants-2014_11
Patent number
US08877774B2

Linked notes

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