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

HRID 1293576Notes

Reaction equation

HRID 1293576 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-3dfefe529c7e4d4a8c267b62b3e71eba
Source dataset
uspto-grants-2007_07
Patent number
US07238818B2

Reaction notes

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