Hydrochloric Acid → 3,5-Bis[(2-methylphenyl)methylidene]thian-4-one

HRID 1704728Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1704728
[S:1]1[CH2:6][CH2:5][C:4](=[O:7])[CH2:3][CH2:2]1.[C:8]1([CH3:16])[C:9]([CH:14]=O)=[CH:10][CH:11]=[CH:12][CH:13]=1.Cl>C(O)C>[CH3:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[CH:16]=[C:3]1[C:4](=[O:7])[C:5](=[CH:16][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH3:14])[CH2:6][S:1][CH2:2]1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 107222-MethylbenzaldehydeHCID 66173Tetrahydrothiopyran-4-one

Produkt 1

HCID 543246713,5-Bis[(2-methylphenyl)methylidene]thian-4-oneAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Tetrahydro-4H-thiopyran-4-one (9.3 g, 0.08 mole) and o-tolualdehyde (25 g, 0.20 mole) are dissolved in 60 ml of ethanol and treated with concentrated hydrochloric acid (6 ml). After heating at reflux temperature for 4 hours, the mixture is cooled and product is collected by filtration. The combined filtrate and washings (ethanol) are concentrated to the original volume and additional concentrated hydrochloric acid (4 ml) is added and the mixture is refluxed for 4 hours. This procedure is repeated 3 times. The combined crude material (23 g) is recrystallized from chloroform/ethanol/H2O to give 22.5 g (88%) of product, m.p. 123°-125°.

Aufarbeitung

  1. temperatureAfter heating
  2. temperatureat reflux temperature for 4 hours
  3. temperaturethe mixture is cooled
  4. filtrationproduct is collected by filtration
  5. concentrationThe combined filtrate and washings (ethanol) are concentrated to the original volume and additional concentrated hydrochloric acid (4 ml)
  6. additionis added
  7. temperaturethe mixture is refluxed for 4 hours
  8. customis recrystallized from chloroform/ethanol/H2O

Quellen und Nachweise

ORD-Eintrag
ord-3f841df869c04f80a9243eeb8dd830bc
Quelldatensatz
uspto-grants-1978_11
Patentnummer
US04127667

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