Acetone → 2-Hydroxy-2-methyl-5-phenylpentane

HRID 484370

Reaktionsgleichung

Reaktionsgleichung von HRID 484370
[Mg].Br[CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:12][C:13]([CH3:15])=[O:14].OS(O)(=O)=O>CCOCC>[CH3:12][C:13]([OH:14])([CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH3:15]

Komponenten

6

Edukt 4

HCID 180AcetoneHCID 1118Sulfuric AcidHCID 12503(3-Bromopropyl)benzeneHCID 5462224Magnesium

Produkt 1

HCID 3464292-Hydroxy-2-methyl-5-phenylpentane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

A mixture of 8.8 g. (0.37 mol.) of magnesium turnings and 150 ml of dry ether was placed in a 3-necked flask fitted with a nitrogen inlet, a reflux condenser and an addition funnel containing 73.7 g (0.37 mol) of 1-bromo-3-phenylpropane. A small amount of the bromo compound was added to the reaction mixture and the mixture warmed in order to initiate reaction. The reaction mixture was treated with 150 ml of dry ether and then the bromo compound was added at such a rate as to maintain gentle reflux. The reaction mixture was heated at reflux for a further 15 minutes and then treated slowly with 21.5 g (0.37 mol) of acetone. The mixture was heated at reflux for a further 30 minutes, cooled and then poured slowly into 300 g of crushed ice. The resultant white precipitate was dissolved by the addition of 20% H2SO4. The organic layer was separated and the aqueous layer extracted with ether. The organic extracts were combined and washed with water and saturated NaCl solution and then dried (MgSO4). The solution was filtered and the solvent removed in-vacuo. The residue was distilled (120° C.; 6 mm) to give the captioned compound as a colorless oil. PMR (CDCl3): δ 1.18 (6H, s), 1.44-1.53 (2 H, m), 1.62-1.72 (2H, m), 2.61 (2H, t, J~7.6 Hz), 7.16-7.30 (5H, m).

Aufarbeitung

  1. additionA mixture of 8.8 g
  2. customfitted with a nitrogen inlet, a reflux condenser and an addition funnel
  3. temperaturethe mixture warmed in order
  4. customreaction
  5. temperatureto maintain gentle reflux
  6. temperatureThe reaction mixture was heated
  7. temperatureat reflux for a further 15 minutes
  8. temperatureThe mixture was heated
  9. temperatureat reflux for a further 30 minutes
  10. temperaturecooled
  11. customThe organic layer was separated
  12. extractionthe aqueous layer extracted with ether
  13. washwashed with water and saturated NaCl solution
  14. dry with materialdried (MgSO4)
  15. filtrationThe solution was filtered
  16. customthe solvent removed in-vacuo
  17. distillationThe residue was distilled (120° C.; 6 mm)

Quellen und Nachweise

ORD-Eintrag
ord-64b5bce29acc4e93ae296a28e6491bef
Quelldatensatz
uspto-grants-1993_07
Patentnummer
US05231113

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