Hydrochloric Acid → 1-(3-(Trimethylsilyl)phenyl)ethanone

HRID 1870538Notes

Reaction equation

HRID 1870538 reaction equation
[CH3:1][Si:2]([CH3:16])([CH3:15])[C:3]1[CH:4]=[C:5]([C:9]2([CH3:14])OCC[O:10]2)[CH:6]=[CH:7][CH:8]=1.Cl>CC(C)=O>[CH3:15][Si:2]([CH3:1])([CH3:16])[C:3]1[CH:4]=[C:5]([C:9](=[O:10])[CH3:14])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 186966022-[3-(Trimethylsilyl)phenyl]-2-methyl-1,3-dioxolane

Product 1

HCID 117454861-(3-(Trimethylsilyl)phenyl)ethanoneYield 97.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of the title compound of Step B (11.2 g) in acetone (400 mnL) was added an aqueous solution of 1N hydrochloric acid (6 mL) and the mixture was heated at reflux overnight. After cooling, the mixture was concentrated under reduced pressure and the resulting residue was dissolved in diethyl ether and dried (MgSO4). The drying agent was removed by filtration and the solvent was removed under reduced pressure to give a yellow oil. The crude product was combined with another batch of crude product prepared in the same manner and purified by distillation (47 Pa, 58-59° C.) to afford 8.9 g of the title compound of Step C as an oil. 1H NMR (CDCl3): δ 8.11 (s,1H), 7.92 (d,1H), 7.7 (d,1H), 7.47 (t,1H), 2.62 (s,3H), 0.30 (s,8H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux overnight
  3. temperatureAfter cooling
  4. concentrationthe mixture was concentrated under reduced pressure
  5. dissolutionthe resulting residue was dissolved in diethyl ether
  6. dry with materialdried (MgSO4)
  7. customThe drying agent was removed by filtration
  8. customthe solvent was removed under reduced pressure
  9. customto give a yellow oil
  10. customprepared in the same manner
  11. distillationpurified by distillation (47 Pa, 58-59° C.)

Sources & evidence

ORD record
ord-e7720ad00a214ebe85bf04e88de2eb4d
Source dataset
uspto-grants-2000_08
Patent number
US06096895

Reaction notes

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