Thionyl Chloride → (3-Acetyloxy-5-carbonochloridoylphenyl) acetate

HRID 239605

Reaktionsgleichung

Reaktionsgleichung von HRID 239605
[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([O:14][C:15](=[O:17])[CH3:16])[CH:13]=1)[C:8](O)=[O:9])(=[O:3])[CH3:2].S(Cl)([Cl:20])=O>C(Cl)Cl>[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([O:14][C:15](=[O:17])[CH3:16])[CH:13]=1)[C:8]([Cl:20])=[O:9])(=[O:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 24386Thionyl Chloride2×HCID 5398693,5-Diacetoxybenzoic Acid

Produkt 1

HCID 11368883(3-Acetyloxy-5-carbonochloridoylphenyl) acetateAusbeute 98,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A 250 ml three-necked flask with magnetic stirrer, thermometer and condenser was charged with 15.4 g (64.7 mmol) of 3,5-diacetoxybenzoic acid, 10 ml of thionyl chloride and 80 ml of CH2Cl2. The mixture was refluxed for 3-5 hours. Then the solvent and remaining thionyl chloride were distilled off. Fresh CH2Cl2 was added and distilled off again. The crude solid was dissolved in 120 ml toluene, and the solution was filtered. Evaporated the solvent out and dried the product at room temperature under 1 mbar. 16.3 g of 3,5-diacetoxybenzoyl chloride were obtained as a white solid. The yield was 98.2%.

Aufarbeitung

  1. temperatureThe mixture was refluxed for 3-5 hours
  2. distillationwere distilled off
  3. additionFresh CH2Cl2 was added
  4. distillationdistilled off again
  5. dissolutionThe crude solid was dissolved in 120 ml toluene
  6. filtrationthe solution was filtered
  7. customEvaporated the solvent out
  8. customdried the product at room temperature under 1 mbar

Quellen und Nachweise

ORD-Eintrag
ord-24fdb4eb2a2040dabf29a994a3031217
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642800B2

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