Water → (RS)-2-(2-buten-1-yl)-3,3,6-trimethyl-1-indanone

HRID 264362

Reaktionsgleichung

Reaktionsgleichung von HRID 264362
[CH3:1][C:2]1([CH3:13])[C:10]2[C:5](=[CH:6][C:7]([CH3:11])=[CH:8][CH:9]=2)[C:4](=[O:12])[CH2:3]1.[CH3:14][CH:15](O)[CH:16]=[CH2:17].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>COC(OC)(C)C>[CH2:14]([CH:3]1[C:2]([CH3:13])([CH3:1])[C:10]2[C:5](=[CH:6][C:7]([CH3:11])=[CH:8][CH:9]=2)[C:4]1=[O:12])[CH:15]=[CH:16][CH3:17]

Komponenten

6

Edukt 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 117163-Buten-2-olHCID 5945383,3,6-Trimethyl-1-indanone

Produkt 1

HCID 53745382(RS)-2-(2-buten-1-yl)-3,3,6-trimethyl-1-indanoneAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 64952,2-DimethoxypropaneLösungsmittel

Versuchsvorschrift

A solution of 18.9 g of 3,3,6-trimethyl-1-indanone, 22.4 ml of 3-buten-2-ol and 300 mg of p-toluenesulfonic acid in 200 ml of 2,2-dimethoxy-propane was boiled under reflux for 64 hours on a water separator filled with molecular sieve (0.4 nm, 2 mm pearl shaped). The reaction mixture was subsequently concentrated in a vacuum and purified by column chromatography on silica gel (hexane/ethyl acetate 6:1). In addition to 4.5 g of educt, there were obtained 12.7 g (51%) of (RS)-2-(2-buten-1-yl)-3,3,6-trimethyl-1-indanone as a yellow oil

Aufarbeitung

  1. additionseparator filled with molecular sieve (0.4 nm, 2 mm pearl shaped)
  2. concentrationThe reaction mixture was subsequently concentrated in a vacuum
  3. custompurified by column chromatography on silica gel (hexane/ethyl acetate 6:1)
  4. additionIn addition to 4.5 g of educt

Quellen und Nachweise

ORD-Eintrag
ord-63e5d96943124b7a9e39fe915fba90e3
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05646173

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