Diethyl Ether → 4-(3-Hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one

HRID 2049894Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2049894
[CH3:1][C:2]12[O:8][CH:7]1[CH2:6][CH2:5][C:4]([CH3:10])([CH3:9])[C:3]2=[CH:11][C:12](=O)[CH:13]=[CH2:14].CC[O:18]CC>C[O-].[Na+].[Cl-].[Na+].O>[CH3:1][C:2]1[CH:7]([OH:8])[CH2:6][CH2:5][C:4]([CH3:10])([CH3:9])[C:3]=1[CH:11]=[CH:12][C:13](=[O:18])[CH3:14]

Komponenten

5

Edukt 2

HCID 3283Diethyl EtherHCID 1317117451-(2,6,6-Trimethyl-2,3-epoxy-1-cyclohexylidene)-buten-2-one

Produkt 1

HCID 540347274-(3-Hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 10942334Sodium MethoxideLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

Retro-ionone (1.9 g) was added to a solution of m-chloroperbenzoic acid (2.2 g) dissolved in dichloromethane. This resulted in an exothermic reaction (~40°). After cooling, the mixture was washed with an aqueous sodium carbonate solution dried over MgSO4 and taken to dryness to yield the epoxide, the 1-(2,6,6-Trimethyl-2,3-epoxy-1-cyclohexylidene)-buten-2-one. This epoxide (~2 g) was dissolved in a solution of methanolic sodium methoxide (1.4 Molar; 20 ml) and left at RT for 1/2 hour (instant color change and probably complete reaction). Dilution with ether followed by a brine washing yielded 1-(2,6,6,-trimethyl-3-hydroxy-1-cyclohexen-1-yl)-3-oxo-1-butene, upon chromatography over silica gel.

Aufarbeitung

  1. custominstant color change and probably complete reaction)

Quellen und Nachweise

ORD-Eintrag
ord-193ad518f2804364a1b267bfaffebe13
Quelldatensatz
uspto-grants-1980_04
Patentnummer
USRE030260

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