1-[1-(p-Chlorophenyl)-2,2-dimethoxyethyl]cyclopropane → 1-[1-(p-Chlorophenyl)-2-methoxyvinyl]cyclopropane

HRID 1596822Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1596822
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:14]2[CH2:16][CH2:15]2)[CH:9](OC)[O:10][CH3:11])=[CH:4][CH:3]=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH:14]2[CH2:16][CH2:15]2)=[CH:9][O:10][CH3:11])=[CH:6][CH:7]=1

Komponenten

3

Edukt 1

HCID 120567791-[1-(p-Chlorophenyl)-2,2-dimethoxyethyl]cyclopropane

Produkt 1

HCID 539422601-[1-(p-Chlorophenyl)-2-methoxyvinyl]cyclopropaneAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

Water is azeotropically removed from a solution of p-toluenesulfonic acid monohydrate in toluene (150 g) until the distillate is clear. A solution of 1-[1-(p-chlorophenyl)-2,2-dimethoxyethyl]cyclopropane (24.7 g, 0.1 mol) in toluene is then added to the dried solution at 100° C. The resultant reaction mixture is refluxed for one hour, distilled to remove about 80 g of toluene/methanol, cooled to room temperature, treated with sodium carbonate (1 g), and poured into a saturated bicarbonate solution (100 mL). The organic phase is separated, washed with water, dried over anhydrous magnesium sulfate, and concentrated in vacuo to give the title product (20 g, 96% yield).

Aufarbeitung

  1. customWater is azeotropically removed from a solution of p-toluenesulfonic acid monohydrate in toluene (150 g) until the distillate
  2. customThe resultant reaction mixture
  3. temperatureis refluxed for one hour
  4. distillationdistilled
  5. customto remove about 80 g of toluene/methanol
  6. additiontreated with sodium carbonate (1 g)
  7. additionpoured into a saturated bicarbonate solution (100 mL)
  8. customThe organic phase is separated
  9. washwashed with water
  10. dry with materialdried over anhydrous magnesium sulfate
  11. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-86afc276550049a3915e71a4d9463045
Quelldatensatz
uspto-grants-2001_09
Patentnummer
US06291721B1

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