4-Hydroxybenzaldehyde → 4-[2-(1,3-Dioxolan-2-yl)ethoxy]benzaldehyde

HRID 785

Reaktionsgleichung

Reaktionsgleichung von HRID 785
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.Br[CH2:11][CH2:12][CH:13]1[O:18][CH2:17][CH2:16]C[O:14]1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.C(#N)C>[O:18]1[CH2:17][CH2:16][O:14][CH:13]1[CH2:12][CH2:11][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 1264-HydroxybenzaldehydeHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 5206561,3-Dioxane, 2-(2-bromoethyl)-

Produkt 1

HCID 196934664-[2-(1,3-Dioxolan-2-yl)ethoxy]benzaldehydeAusbeute 104,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

In a 500 ml flask, 120 ml of acetonitrile, 13.8 g of 4-hydroxybenzaldehyde, 19.9 g of 2-(2-bromoethyl)-1,3-dioxane, 1.8 g of potassium iodide, and 35.8 g of potassium carbonate were placed and then, reacted at 80° C. for 5 hr. Thereafter, to the reaction mixture was added 200 ml of ethyl acetate and washed once with a saturated aqueous potassium carbonate solution, distilled water and saturated saline. The washed organic phase was dried over anhydrous magnesium sulfate and the solvent was removed, to give 23.7 g of 4-(2-[1,3]-dioxolan-2-yl-ethoxy)benzaldehyde.

Aufarbeitung

  1. customreacted at 80° C. for 5 hr
  2. washwashed once with a saturated aqueous potassium carbonate solution
  3. distillationdistilled water and saturated saline
  4. dry with materialThe washed organic phase was dried over anhydrous magnesium sulfate
  5. customthe solvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-ab767623531e408bb0c0320b5128145a
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05723258

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