p-Toluenesulfonic acid → beta-Damascenone

HRID 1156628

Reaktionsgleichung

Reaktionsgleichung von HRID 1156628
[CH3:1][C:2]1[CH:7]=[CH:6][CH2:5][C:4]([CH3:9])([CH3:8])[C:3]=1[C:10]#[C:11][CH:12](OC(=O)C)[CH3:13].C(Cl)Cl.C1(C)C=CC(S(O)(=O)=[O:28])=CC=1>O>[C:10]([C:3]1[C:4]([CH3:9])([CH3:8])[CH2:5][CH:6]=[CH:7][C:2]=1[CH3:1])(=[O:28])/[CH:11]=[CH:12]/[CH3:13]

Komponenten

5

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 6344DichloromethaneHCID 155179992,6,6-Trimethyl-1-(3-acetoxy-but-1-ynyl)cyclohexa-1,3-diene

Produkt 1

HCID 5366074beta-DamascenoneAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

In a 100 ml. three-necked flask fitted with a mechanical stirrer and a Dean-Stark water separator provided with a reflux condenser, a solution of 5 g. of 2,6,6-trimethyl-1-(3-acetoxy-but-1-ynyl)cyclohexa-1,3-diene in 70 ml. of methylene chloride is refluxed while stirring. Then 0.2 g. of p-toluenesulfonic acid is added and the reaction mixture is refluxed for an additional 4 to 5 hours. The reaction mixture is cooled and poured into 70 ml. of water. The organic layer is separated, subsequently washed with 10% sodium bicarbonate solution and water, and finally dried over sodium sulfate. Concentration yields 5 g. of a residue which gives on distillation 2.5 g. or 60% yield of 1-crotonoyl-2,6,6-trimethylcyclohexa-1,3-diene, b.p. 75°-80° C./0.1 mm., nD20 1.5150.

Aufarbeitung

  1. customthree-necked flask fitted with a mechanical stirrer
  2. temperaturethe reaction mixture is refluxed for an additional 4 to 5 hours
  3. temperatureThe reaction mixture is cooled
  4. additionpoured into 70 ml
  5. customThe organic layer is separated
  6. washsubsequently washed with 10% sodium bicarbonate solution and water
  7. dry with materialfinally dried over sodium sulfate
  8. concentrationConcentration
  9. customyields 5 g
  10. customof a residue which gives on distillation 2.5 g

Quellen und Nachweise

ORD-Eintrag
ord-a64505eab20c471698fe48cb14dc934b
Quelldatensatz
uspto-grants-1982_06
Patentnummer
US04336401

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