Acetic Acid → 5,5'-(Hexane-2,5-diylidene)di(cyclopenta-1,3-diene)

HRID 1603975Notes

Reaction equation

HRID 1603975 reaction equation
[CH3:1][C:2](=O)[CH2:3][CH2:4][C:5](=O)[CH3:6].[CH:9]1[CH2:13][CH:12]=[CH:11][CH:10]=1.N1[CH2:18][CH2:17][CH2:16][CH2:15]1.[C:19](O)(=O)C>CO.O>[C:10]1(=[C:2]([CH2:3][CH2:4][C:5](=[C:6]2[CH:18]=[CH:17][CH:16]=[CH:15]2)[CH3:19])[CH3:1])[CH:9]=[CH:13][CH:12]=[CH:11]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7612CyclopentadieneHCID 80352,5-HexanedioneHCID 31268Pyrrolidine

Product 1

HCID 149519975,5'-(Hexane-2,5-diylidene)di(cyclopenta-1,3-diene)

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

In a modified reaction procedure [a], 11.0 g (96.3 mmol) of 2,5-hexanedione and 12.7 g (193 mmol) of freshly cracked cyclopentadiene are dissolved in 60 ml of methanol, the solution is cooled to 0° C., and 8.60 g (121 mmol) of pyrrolidine are added. The reaction solution is stirred at 0° C. for 90 minutes, hydrolyzed using 5 ml of glacial acetic acid and 50 ml of water, and extracted twice with 70 ml of diethyl ether in each case, and the combined organic phases are washed with saturated sodium chloride solution and dried over magnesium sulfate, giving, after removal of the solvent in vacuo, 18.0 g (89%) of the difulvene as an orange-red, oily residue.

Workup

  1. extractionextracted twice with 70 ml of diethyl ether in each case
  2. washthe combined organic phases are washed with saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. customgiving
  5. customafter removal of the solvent in vacuo, 18.0 g (89%) of the difulvene as an orange-red, oily residue

Sources & evidence

ORD record
ord-6346eddff8c44b5dbd91e3c7c2ca503a
Source dataset
uspto-grants-1999_11
Patent number
US05990254

Reaction notes

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