Methyl Salicylate → Methyl 5-acetylsalicylate

HRID 596989

Reaktionsgleichung

Reaktionsgleichung von HRID 596989
[C:1]([O:10][CH3:11])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[C:12](Cl)(=[O:14])[CH3:13].[Cl-].[Al+3].[Cl-].[Cl-]>ClC(Cl)=C(Cl)Cl>[C:12]([C:7]1[CH:8]=[C:2]([C:1]([O:10][CH3:11])=[O:9])[C:3]([OH:4])=[CH:5][CH:6]=1)(=[O:14])[CH3:13]

Komponenten

5

Edukt 3

HCID 4133Methyl SalicylateHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 85444Methyl 5-acetylsalicylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31373TetrachloroethyleneLösungsmittel2×

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

A solution of 75 g. (0.5 m.) of methyl salicylate in 200 ml. of tetrachloroethylene is cooled in an ice bath and treated with a solution of 40 g. (0.5 m.) of acetyl chloride in 200 ml. of tetrachloroethylene. To the chilled mixture is added 133 g. (1.0 m.) of aluminum chloride over a fifteen minute period, maintaining the temperature below 25° C. After the adddition is completed the mixture is stirred for 4 hours at 25° C. and then poured into ice water. The organic layer is separated, washed with water and saturated aqueous sodium bicarbonate solution, dried and evaporated. The residual oil is crystallized from hexane to give methyl 5-acetylsalicylate, m.p. 60°-62° C.

Aufarbeitung

  1. additiontreated with a solution of 40 g
  2. additionTo the chilled mixture is added 133 g
  3. temperaturemaintaining the temperature below 25° C
  4. customThe organic layer is separated
  5. washwashed with water and saturated aqueous sodium bicarbonate solution
  6. customdried
  7. customevaporated
  8. customThe residual oil is crystallized from hexane

Quellen und Nachweise

ORD-Eintrag
ord-8f5ce8c41c0545949d547f7e11c55f7a
Quelldatensatz
uspto-grants-1977_03
Patentnummer
US04012528

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