Hexane → (2-Methyl-3-phenylphenyl)methyl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate

HRID 1607351

Reaktionsgleichung

Reaktionsgleichung von HRID 1607351
[CH3:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:14][OH:15].[CH3:16][C:17]1([CH3:27])[CH:19]([CH:20]=[C:21]([CH3:23])[CH3:22])[CH:18]1[C:24](Cl)=[O:25].CCCCCC>N1C=CC=CC=1.C(OCC)C>[CH3:16][C:17]1([CH3:27])[CH:19]([CH:20]=[C:21]([CH3:22])[CH3:23])[CH:18]1[C:24]([O:15][CH2:14][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:2]=1[CH3:1])=[O:25]

Komponenten

6

Edukt 3

HCID 8058HexaneHCID 26620(1R-trans)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarbonyl chlorideHCID 596875[1,1'-Biphenyl]-3-methanol, 2-methyl-

Produkt 1

HCID 13933694(2-Methyl-3-phenylphenyl)methyl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylateAusbeute 80,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

A solution of 2.97 g (15.0 mmol) of (2-methyl-3phenylphenyl)methanol in 1.5 ml of pyridine and 10 ml of diethyl ether, was dropwise added to a solution of 2.80 g (15.0 mmol) of 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarbonyl chloride in 10 ml of diethyl ether, and the mixture was stirred at room temperature for 3 hours. After an addition of 20 ml of hexane thereto, the inorganic salt was filtered off, and the filtrate was concentrated under reduced pressure. The product was purified by column chromatography (silica gel, dichloromethane/hexane=1/2) to obtain 4.23 g of (2-methyl-3-phenylphenyl)methyl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate as a colorless oil.

Aufarbeitung

  1. filtrationthe inorganic salt was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe product was purified by column chromatography (silica gel, dichloromethane/hexane=1/2)

Quellen und Nachweise

ORD-Eintrag
ord-a77edb3fb18444be9245c48ecc90efb5
Quelldatensatz
uspto-grants-1989_09
Patentnummer
US04864052

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