Hydrochloric Acid → 2-(3,4-Dimethoxyphenyl)-m-dithiane-2-propionic acid

HRID 1415275

Reaktionsgleichung

Reaktionsgleichung von HRID 1415275
[C:1]([CH2:13][CH2:14][C:15]([OH:17])=[O:16])(=O)[C:2]1[CH:11]=[CH:10][C:7]([O:8][CH3:9])=[C:4]([O:5][CH3:6])[CH:3]=1.[CH2:18]([SH:22])[CH2:19][CH2:20][SH:21].Cl>C(Cl)(Cl)Cl>[CH3:6][O:5][C:4]1[CH:3]=[C:2]([C:1]2([CH2:13][CH2:14][C:15]([OH:17])=[O:16])[S:22][CH2:18][CH2:19][CH2:20][S:21]2)[CH:11]=[CH:10][C:7]=1[O:8][CH3:9]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 80131,3-PropanedithiolHCID 2193904-(3,4-Dimethoxyphenyl)-4-oxobutanoic acid

Produkt 1

HCID 227583982-(3,4-Dimethoxyphenyl)-m-dithiane-2-propionic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

50 g of 3-veratroylpropionic acid in 400 ml of chloroform and 22.7 g of 1,3-propanedithiol are treated with hydrogen chloride up to saturation while stirring. After 3 hours at room temperature, the solution is evaporated to 50 ml and diluted with ether. The resulting solution is extracted three times with 5% sodium carbonate. The basic phases are combined and made acidic with concentrated hydrochloric acid. The precipitated product is extracted with ether/methylene chloride (1:3). The organic extracts are dried and evaporated. The residue is recrystallized from ethanol, there being obtained 2-(3,4-dimethoxyphenyl)-m-dithiane-2-propionic acid of melting point 134°-135° C.

Aufarbeitung

  1. customthe solution is evaporated to 50 ml
  2. additiondiluted with ether
  3. extractionThe resulting solution is extracted three times with 5% sodium carbonate
  4. extractionThe precipitated product is extracted with ether/methylene chloride (1:3)
  5. customThe organic extracts are dried
  6. customevaporated
  7. customThe residue is recrystallized from ethanol, there

Quellen und Nachweise

ORD-Eintrag
ord-ad9f231091b04e5b95e5b03240479864
Quelldatensatz
uspto-grants-1977_01
Patentnummer
US04003914

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