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

HRID 1167350Notes

Reaction equation

HRID 1167350 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(S(O)(=O)=O)=CC=1>C1(C)C=CC=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 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 27335536-Bromo-2-tetralone

Product 1

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

Reagents, catalysts & solvents 1

HCID 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 tohuene 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 tohuene 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-ccfabb99b17a4f42bf966282ca917bfc
Source dataset
uspto-grants-2003_09
Patent number
US06617347B1

Reaction notes

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