4-(Bromomethyl)-2,2-dimethyl-1,3-dioxolane → (2,2-Dimethyl-1,3-dioxolan-4-yl)methyl benzoate

HRID 1857061

Reaktionsgleichung

Reaktionsgleichung von HRID 1857061
[C:1]([O-:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na+].Br[CH2:12][CH:13]1[CH2:17][O:16][C:15]([CH3:19])([CH3:18])[O:14]1>CN(C)C=O>[C:1]([O:9][CH2:12][CH:13]1[CH2:17][O:16][C:15]([CH3:19])([CH3:18])[O:14]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 1697594-(Bromomethyl)-2,2-dimethyl-1,3-dioxolaneHCID 517055Sodium Benzoate

Produkt 1

HCID 571151(2,2-Dimethyl-1,3-dioxolan-4-yl)methyl benzoateAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

Then, sodium benzoate (50.44 g, 0.35 mol) were added to a mixture of 4-bromomethyl-2,2-dimethyl-1,3-dioxolane (58.52 g, 0.3 mol) and N,N-dimethylformamide (500 ml) and the resulting mixture was stirred for 15 hours at 150° C. After cooling the salt was filtered and N,N-dimethylformamide was removed in vacuo and water was added to the residue and extracted with toluene. The extract was washed with saturated brine, dried over anhydrous sodium sulfate and condensed in vacuo to give 64.5 g of crude 4-benzoyloxymethyl-2,2-dimethyl-1,3-dioxolane (yield 91%).

Aufarbeitung

  1. temperatureAfter cooling the salt
  2. filtrationwas filtered
  3. customN,N-dimethylformamide was removed in vacuo and water
  4. additionwas added to the residue
  5. extractionextracted with toluene
  6. washThe extract was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate and condensed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b283fed5cf0f464faa6011368a0141de
Quelldatensatz
uspto-grants-2000_11
Patentnummer
US06143908

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