Ethylene Glycol → HCID 45158897, compound

HRID 2377232Notes

Reaction equation

HRID 2377232 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:23](O)[CH2:24][OH:25]>C1C=CC=CC=1>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]32[O:25][CH2:24][CH2:23][O:11]3)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 1397781-Indanone, 6-bromo-

Product 1

HCID 45158897HCID 45158897, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of Example 3 (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 heated to reflux for about 24 hours, using a Dean-Stark trap to separate the forming 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 (MgSO4), filtered and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel using dichloromethane as the mobile phase to provide the desired product. MS (DCI-NH3): m/z 254, 256 (M)+.

Workup

  1. temperatureto reflux for about 24 hours
  2. customto separate the forming 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 (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum
  10. customThe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-034d53a8dc874815b5039fd7bb8d1fd6
Source dataset
uspto-grants-2008_12
Patent number
US07468371B2

Reaction notes

Loading…