p-Toluenesulfonic acid → beta-Damascenone

HRID 1156629

Reaktionsgleichung

Reaktionsgleichung von HRID 1156629
[CH3:1][C:2]1[CH:7](OC(=O)C)[CH2:6][CH2:5][C:4]([CH3:13])([CH3:12])[C:3]=1[C:14]#[C:15][CH:16](OC(=O)C)[CH3:17].C(Cl)Cl.C1(C)C=CC(S(O)(=O)=[O:32])=CC=1>O>[C:14]([C:3]1[C:4]([CH3:13])([CH3:12])[CH2:5][CH:6]=[CH:7][C:2]=1[CH3:1])(=[O:32])/[CH:15]=[CH:16]/[CH3:17]

Komponenten

5

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 6344DichloromethaneHCID 205354732,6,6-Trimethyl-3-acetoxy-1-(3-acetoxy-but-1-ynyl)cyclohex-1ene

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 7 g. of 2,6,6-trimethyl-3-acetoxy-1-(3-acetoxy-but-1-ynyl)cyclohex-1ene in 70 ml. of methylene chloride is refluxed while stirring. Then 0.7 g. of p-toluenesulfonic acid is added and the reaction mixture is refluxed for an additional 7 hours. The reaction mixture is cooled and then poured into 70 ml. of water. The organic layer is separated, washed with 10% sodium bicarbonate solution and water. Drying over sodium sulfate and subsequent concentration yields 5 g. of a residue which gives, upon distillation using a short Vigreux column, 3 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 7 hours
  3. temperatureThe reaction mixture is cooled
  4. additionpoured into 70 ml
  5. customThe organic layer is separated
  6. washwashed with 10% sodium bicarbonate solution and water
  7. dry with materialDrying over sodium sulfate and subsequent concentration
  8. customyields 5 g
  9. customof a residue which gives, upon distillation

Quellen und Nachweise

ORD-Eintrag
ord-cabe6f786e8949c58a514021a7b02f61
Quelldatensatz
uspto-grants-1982_06
Patentnummer
US04336401

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