Acetone → 2-tert-Butyl-5-(propan-2-ylidene)cyclopenta-1,3-diene

HRID 2263663Notes

Reaction equation

HRID 2263663 reaction equation
[CH3:1][C:2]([CH3:4])=O.[C:5]([C:9]1[CH2:13][CH:12]=[CH:11][CH:10]=1)([CH3:8])([CH3:7])[CH3:6].C(O)C.[OH-].[K+]>CCOCC>[C:5]([C:9]1[CH:13]=[CH:12][C:11](=[C:2]([CH3:4])[CH3:1])[CH:10]=1)([CH3:8])([CH3:7])[CH3:6]

Participants

6

Reactant 4

HCID 180AcetoneHCID 702EthanolHCID 14797Potassium HydroxideHCID 633714Tert-butylcyclopentadiene

Product 1

HCID 146882832-tert-Butyl-5-(propan-2-ylidene)cyclopenta-1,3-diene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Dry acetone (99.3 mmol, 5.77 g, 7.3 mL) and t-butylcyclopentadiene (50.6 mmol, 6.17 g) were mixed in a dropping funnel and added at room temperature to an ethanol solution (10 mL) of KOH (10.3 mmol, 0.58 g) stirring under nitrogen. After stirring overnight, the golden solution was diluted with ether, washed with 2 N HCl, water, and dried over sodium sulfate. A sample of the crude organic fraction (7.4 g) was taken for analysis (GCMS) showing 90% conversion to the title compound. The product was submitted to distillation. 1H-NMR (CDCl3): δ 1.38 (s, 9H), 2.28 (s, 6H), 6.24 (m, 1H), 6.63 (m, 2H).

Workup

  1. stirringAfter stirring overnight
  2. washwashed with 2 N HCl, water
  3. dry with materialdried over sodium sulfate
  4. distillationThe product was submitted to distillation

Sources & evidence

ORD record
ord-e8607b2a98ed4e35908ed7483b1b362b
Source dataset
uspto-grants-2010_12
Patent number
US07851644B2

Reaction notes

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