Ethylene Glycol → 2-Methyl-2-(4-methylphenyl)-1,3-dioxolane

HRID 250522

Reaktionsgleichung

Reaktionsgleichung von HRID 250522
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:10])=[O:9])=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:22](O)[CH2:23][OH:24]>C1(C)C=CC=CC=1>[CH3:10][C:8]1([C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)[O:24][CH2:23][CH2:22][O:9]1

Komponenten

5

Edukt 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 8500p-METHYLACETOPHENONE

Produkt 1

HCID 27554692-Methyl-2-(4-methylphenyl)-1,3-dioxolaneAusbeute 79,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 4-methylacetophenone (1.00 g, 7.45 mmol), p-toluenesulfonic acid (133 mg, 0.745 mmol) and ethylene glycol (1.20 mL, 22.4 mmol) in dry toluene (20 mL) was heated at reflux with a Dean-Stark apparatus under nitrogen for 24 h. The mixture was allowed to cool to room temperature and the solvent was evaporated in vacuo. The residue was taken up in ether (20 mL) and the solution was washed with saturated sodium bicarbonate solution (2×10 mL) and brine (1×10 mL), then dried (Na2SO4) and concentrated under reduced pressure. Flash column chromatography of the residue, eluting with 37% aqueous ammonia:ether:hexane (0.02:1:6) afforded 2-methyl-2-(4-methylphenyl)-1,3-dioxolane (23) as a colourless oil (1.05 g, 59%). 1H nmr (200 MHz, CDCl3) 1.65 (s, 3H, CH3), 2.35 (s, 3H, ArCH3), 3.74-3.86 (m, 2H, OCH2), 3.94-4.06 (m, 2H, OCH2), 7.15 (d, J=8.2 Hz, 2H, 2×ArH), 7.37 (d, J=8.2 Hz, 2H, 2×ArH).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux with a Dean-Stark apparatus under nitrogen for 24 h
  3. customthe solvent was evaporated in vacuo
  4. washthe solution was washed with saturated sodium bicarbonate solution (2×10 mL) and brine (1×10 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. washFlash column chromatography of the residue, eluting with 37% aqueous ammonia:ether:hexane (0.02:1:6)

Quellen und Nachweise

ORD-Eintrag
ord-125d60b86bf04bc18b8c7532c6023856
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863313B2

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