p-METHYLACETOPHENONE → 6-Methyl-6-(p-tolyl)fulvene

HRID 630583Notes

Reaction equation

HRID 630583 reaction equation
[CH:1]1([Li])[CH:5]=[CH:4][CH:3]=[CH:2]1.[CH3:7][C:8]1[CH:13]=[CH:12][C:11]([C:14](=O)[CH3:15])=[CH:10][CH:9]=1>C(OCC)C>[CH3:15][C:14]([C:11]1[CH:12]=[CH:13][C:8]([CH3:7])=[CH:9][CH:10]=1)=[C:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 8500p-METHYLACETOPHENONEHCID 178506819HCID 178506819, compound

Product 1

HCID 216764486-Methyl-6-(p-tolyl)fulveneYield 72.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Under a nitrogen atmosphere, a solution of a cyclopentadienyllithium salt (5.9 g, 81.9 mmol) in dry diethyl ether (100 mL) was cooled in an ice bath, and 4′-methylacetophenone (10.0 g, 74.5 mmol) was dropped thereinto. Then, the product was stirred at room temperature for 20 hours to induce a reaction. After the reaction was terminated, dilute aqueous hydrochloric acid was added thereto, the product was subjected to extraction with hexane, the organic layer was subsequently washed with water and then dehydrated with anhydrous magnesium sulfate, and then the solvent was distilled off to produce a red liquid. The red liquid was purified by column chromatography (silica gel, solvent: hexane) to produce 9.8 g of 6-methyl-6-(p-tolyl)fulvene. The analytical values were as follows.

Workup

  1. customa reaction
  2. customAfter the reaction was terminated
  3. additiondilute aqueous hydrochloric acid was added
  4. extractionthe product was subjected to extraction with hexane
  5. washthe organic layer was subsequently washed with water
  6. distillationthe solvent was distilled off
  7. customto produce a red liquid
  8. customThe red liquid was purified by column chromatography (silica gel, solvent: hexane)

Sources & evidence

ORD record
ord-363bbf808c1048a68d73c3ab3d036d24
Source dataset
uspto-grants-2016_04
Patent number
US09315602B2

Reaction notes

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