Ethanol → Sodium

HRID 1611898Notes

Reaction equation

HRID 1611898 reaction equation
C(O)C.[Na:4].[CH:5]1[CH2:9][CH:8]=[CH:7][CH:6]=1.O.[CH3:11][CH2:12][CH2:13][CH2:14][CH3:15]>>[Na:4].[CH2:14]([CH:15]=[C:6]1[CH:5]=[CH:9][CH:8]=[CH:7]1)[CH2:13][CH:12]=[CH2:11]

Participants

7

Reactant 5

HCID 702Ethanol2×HCID 962WaterHCID 7612CyclopentadieneHCID 8003PentaneHCID 5360545Sodium

Product 2

HCID 5360545SodiumHCID 18676316HCID 18676316, compound

Conditions

Temperature
0 °C

Procedure

Then a sodium solution of ethanol was prepared by combining 4.3 g of sodium with 150 mL of ethanol. The solution was cooled to 0° C. and then 30 g of the phenyl alkenyl ketone was added. Then 30 mL of cyclopentadiene was slowly added to the solution and the mixture stirred for 4 hrs. Then 100 mL of water and 100 mL of pentane were added. The ethanol-water layer was then extracted twice with pentane. The organic layer was dried over filtered silica and the solvent removed in a vacuum to yield 6-phenyl, 6-(but-3-enyl) fulvene.

Workup

  1. extractionThe ethanol-water layer was then extracted twice with pentane
  2. customThe organic layer was dried
  3. filtrationover filtered silica
  4. customthe solvent removed in a vacuum

Sources & evidence

ORD record
ord-aec4113130534069afd56b008f6c875a
Source dataset
uspto-grants-2006_01
Patent number
US06992035B2

Reaction notes

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