p-Toluenesulfonic acid → HCID 10464631, Verbindung

HRID 868332

Reaktionsgleichung

Reaktionsgleichung von HRID 868332
C([C:6]1[C:7](=[O:17])[O:8][C:9]2[C:14](C=1)=CC=C(O)C=2)(OCC)=O.[CH2:18]([O:20][CH:21]=[CH2:22])[CH3:19].C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH-].[K+]>C(Cl)Cl>[CH2:18]([O:20][CH:21]([O:17][CH:7]([O:8][CH2:9][CH3:14])[CH3:6])[CH3:22])[CH3:19]

Komponenten

6

Edukt 4

HCID 6101p-Toluenesulfonic acidHCID 8023Ethyl vinyl etherHCID 14797Potassium HydroxideHCID 52896133-Carbethoxyumbeliferone

Produkt 1

HCID 10464631HCID 10464631, VerbindungAusbeute 26 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a slurry of 5.0 g (21 mMol) of 3-carbethoxy-7-hydroxycoumarin [H. Pechmann and E. Graezer, Chem. Ber. 34:378 (1901)9 in 100 mL of CH2Cl2 containing 5 mL of ethylvinyl ether was added 30 mg of p-toluenesulfonic acid. After 15 minutes, the reaction was poured into 100 mL of 10% potassium hydroxide (KOH) solution. The organic phase was separated, washed with H2O, dried and evaporated. The residue was taken up in toluene and precipitated with hexane to give 1.73 g (26% yield) of the 1-ethoxyethyl ether as a solid, m.p. 70°-71° C.

Aufarbeitung

  1. customThe organic phase was separated
  2. washwashed with H2O
  3. customdried
  4. customevaporated
  5. customprecipitated with hexane

Quellen und Nachweise

ORD-Eintrag
ord-82a87649d46841e3b32d2c033f6b74a2
Quelldatensatz
uspto-grants-1988_10
Patentnummer
US04778893

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