Benzaldehyde → 4-Butyl-2-phenyl-1,3-dioxolane

HRID 651042

Reaktionsgleichung

Reaktionsgleichung von HRID 651042
[CH:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:9](O)[CH:10]([OH:15])[CH2:11][CH2:12][CH2:13][CH3:14]>C1(C)C=CC=CC=1.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>[CH2:11]([CH:10]1[O:15][CH:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[O:8][CH2:9]1)[CH2:12][CH2:13][CH3:14]

Komponenten

5

Edukt 2

HCID 240BenzaldehydeHCID 943351,2-Hexanediol

Produkt 1

HCID 217105764-Butyl-2-phenyl-1,3-dioxolaneAusbeute 102,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-KatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of benzaldehyde (5.1 mL, 50.0 mmol), 1,2-hexanediol (6.5 g, 55.0 mmol), and camphorsulfonic acid (0.58 g, 2.5 mmol) in 50 mL of toluene was heated to reflux (Dean-Stark) with azeotropic removal of water. When the theoretical amount of water was distilled (4.5 hours), the mixture was cooled to room temperature and diluted with 80 mL of ether. The solution was extracted with 2M aqueous sodium carbonate, water and brine, dried (Na2SO4), filtered, and concentrated to provide 10.54 g (102%) of the title compound.

Aufarbeitung

  1. temperatureto reflux (Dean-Stark)
  2. customwith azeotropic removal of water
  3. distillationWhen the theoretical amount of water was distilled (4.5 hours)
  4. additiondiluted with 80 mL of ether
  5. extractionThe solution was extracted with 2M aqueous sodium carbonate, water and brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-50e9d02e287546d8aa1ddab3807cf092
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06277871B1

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