Ethylene Glycol → 6-Bromo-2-tetralone ethylene ketal

HRID 1601466Notes

Reaction equation

HRID 1601466 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][C:7](=[O:12])[CH2:6][CH2:5]2.[CH2:13](O)[CH2:14][OH:15]>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:14]1[O:15][C:7]2([CH2:6][CH2:5][C:4]3[C:9](=[CH:10][CH:11]=[C:2]([Br:1])[CH:3]=3)[CH2:8]2)[O:12][CH2:13]1

Participants

5

Reactant 2

HCID 174Ethylene GlycolHCID 27335536-Bromo-2-tetralone

Product 1

HCID 233778946-Bromo-2-tetralone ethylene ketalYield 93.2%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

6-bromo-2-tetralone (2.0 g, 8.89 mmol) was dissolved in toluene (50 mL) and treated with excess ethylene glycol (4.88 mL, 88.9 mmol) and catalytic p-toluenesulfonic acid (15 mg). The solution was stirred at reflux 16 hours, and water was removed from the reaction mixture using a Dean-Stark condenser. After cooling to ambient temperature, the toluene solution was washed 2×1N NaOH, 1×water, 1×brine, dried over Na2SO4 and concentrated in vacuo to give 2.23 g (93%) of 6-bromo-2-tetralone ethylene ketal as a brown oil which was used without further purification.

Workup

  1. temperatureat reflux 16 hours
  2. customwater was removed from the reaction mixture
  3. washthe toluene solution was washed 2×1N NaOH, 1×water, 1×brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a939a7207daf475da36ef428d2df7b23
Source dataset
uspto-grants-1999_11
Patent number
US05977154

Reaction notes

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