Ethylene Glycol → 5-Bromo-1,1-(ethylenedioxo)-indane

HRID 2252261Notes

Reaction equation

HRID 2252261 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:23](O)[CH2:24][OH:25].N>C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7]1([O:25][CH2:24][CH2:23][O:11]1)[CH2:6][CH2:5]2

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 222AmmoniaHCID 6101p-Toluenesulfonic acidHCID 5206955-Bromo-1-indanone

Product 1

HCID 451588945-Bromo-1,1-(ethylenedioxo)-indane

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 5-bromo-1-indanone (13.0 g, 61.8 mmol), p-toluenesulfonic acid (23 mg, 0.12 mmol) and ethylene glycol (27.6 mL, 494.6 mmol) in benzene (140 mL) was refluxed for about 24 hours, using a Dean-Stark trap to remove water. The mixture was cooled, poured into excess 5% aqueous sodium bicarbonate and was extracted with toluene. The combined organic extracts were washed with brine, dried with MgSO4, filtered, and evaporated in vacuum. The residue was purified by flash column chromatography using dichloromethane as the mobile phase to give the above intermediate. MS (DCI/NH3): m/z 254, 256 (M)+.

Workup

  1. temperaturewas refluxed for about 24 hours
  2. customto remove water
  3. temperatureThe mixture was cooled
  4. additionpoured into excess 5% aqueous sodium bicarbonate
  5. extractionwas extracted with toluene
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried with MgSO4
  8. filtrationfiltered
  9. customevaporated in vacuum
  10. customThe residue was purified by flash column chromatography
  11. customto give the above intermediate

Sources & evidence

ORD record
ord-89f48ed5b59a4f4195cf5a3d58126f1e
Source dataset
uspto-grants-2008_01
Patent number
US07320986B2

Reaction notes

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