Ethylene Glycol → 2-(4-Bromobutyl)-2-methyl-1,3-dioxolane

HRID 42750

Reaktionsgleichung

Reaktionsgleichung von HRID 42750
N#N.[Br:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8](=[O:10])[CH3:9].[CH2:11](O)[CH2:12][OH:13].CC1C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1.CCOCC>[Br:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]1([CH3:9])[O:13][CH2:12][CH2:11][O:10]1

Komponenten

8

Edukt 5

HCID 174Ethylene GlycolHCID 947NitrogenHCID 6101p-Toluenesulfonic acidHCID 250616-Bromohexan-2-oneHCID 516892Sodium Bicarbonate

Produkt 1

HCID 5600132-(4-Bromobutyl)-2-methyl-1,3-dioxolane

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

In a flame dried round-bottomed flask equipped with a magnetic stir bar and a Dean-Stark under inert atmosphere (N2), a solution of 6-bromo-hexan-2-one (3.34 g, 18.65 mmol) in toluene (71.3 mL) was treated with ethylene glycol (10.4 mL, 186.92 mmol) and TsOH (35 mg, 0.19 mmol). The reaction mixture was heated to reflux for 3 h, allowed to cool to rt and sat. aq. NaHCO3 (100 mL) and ether (100 mL) were added and the aq. phase was washed with water (2×100 mL), dried over MgSO4, filtered, and the solvents were removed under reduced pressure to give the title compound. 1H NMR (400 MHz, CDCl3) δ1.34 (s, 3H), 1.50-1.65 (m, 2H), 1.65-1.75 (m, 2H), 1.84-1.98 (m, 2H), 3.43 (t, J=6.8 Hz, 2H), 3.90-4.04 (m, 4H).

Aufarbeitung

  1. customIn a flame dried round-bottomed flask equipped with a magnetic stir bar
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux for 3 h
  4. washthe aq. phase was washed with water (2×100 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customthe solvents were removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1f37e5b7d2814e2bb7eb2867e6bdecb9
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536209B2

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