Water → ((cyclohex-2-enyloxy)methyl)benzene

HRID 74985

Reaktionsgleichung

Reaktionsgleichung von HRID 74985
[CH:1]1([OH:7])[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1.[H-].[Na+].[CH2:10](Br)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O>C1COCC1.CCOCC>[CH:1]1([O:7][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1

Komponenten

7

Edukt 4

HCID 962WaterHCID 7498Benzyl BromideHCID 131982-Cyclohexen-1-OLHCID 24758Sodium hydride

Produkt 1

HCID 10867111((cyclohex-2-enyloxy)methyl)benzene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A solution of cyclohex-2-en-1-ol (10.0 g, 101.9 mmol) in anhydrous THF (100 mL) was added to a stirred suspension containing sodium hydride (8.0 g, 199.7 mmol) (60% dispersion in oil) and benzyl bromide in anhydrous THF (250 mL) maintained at 50° C. The resulting solution was stirred at 55-60° C. for 18 h. After cooling to ambient temperature, water was added to quench the reaction and the mixture was diluted with ether (500 mL). The organic phase was separated, dried (Na2SO4), filtered and concentrated in vacuo to an oil that was subjected to a short silica plug filtration to provide 16.1 g of desired product 51a that was used directly in the next step without further purification.

Aufarbeitung

  1. temperatureAfter cooling to ambient temperature
  2. customto quench
  3. customthe reaction
  4. customThe organic phase was separated
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo to an oil that
  8. filtrationwas subjected to a short silica plug filtration

Quellen und Nachweise

ORD-Eintrag
ord-4551983249644db0ac1b7f9159ed7a96
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829007B2

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