Carbon Disulfide → 1,1,3,6,8,8-hexamethyl-1H,8H-dicyclopenta[b,h]fluorene

HRID 1174073Notes

Reaction equation

HRID 1174073 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH:5]1[C:17]2[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]=2[CH:8]=[CH:7][CH:6]=1.C(=S)=S.O=[C:22]([CH:24]=[C:25]([CH3:27])[CH3:26])[CH3:23]>O>[CH3:9][C:17]1([CH3:16])[C:6]2[CH:5]=[C:17]3[C:9]([C:10]4[CH:11]=[C:12]5[C:22]([CH3:23])=[CH:24][C:25]([CH3:27])([CH3:26])[C:13]5=[CH:14][C:15]=4[CH2:16]3)=[CH:8][C:7]=2[C:6]([CH3:7])=[CH:5]1

Participants

6

Reactant 4

HCID 6348Carbon DisulfideHCID 6853FluoreneHCID 8858Mesityl oxideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 586524371,1,3,6,8,8-hexamethyl-1H,8H-dicyclopenta[b,h]fluorene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 300-ml three-neck flask, 25.8 g of anhydrous aluminum chloride, 5.18 g of fluorene, and 200 ml of carbon disulfide were charged under nitrogen atmosphere. 6.18 g of mesityl oxide was added dropwise thereto over 15 minutes in a water bath, and the mixture was stirred for 10 hours under reflux. After standing to cool, 100 ml of water was added thereto, and the organic layer was separated. The aqueous layer was extracted with 300 ml of hexane, and the separated organic layer was combined, and washed with water and a saturated aqueous solution of sodium chloride. After the solution was dried over magnesium sulfate, the solvent was distilled off, and the obtained product was purified by column chromatography, and recrystallized with a mixed solvent of ethanol/hexane. The yield was 1.14 g. Identification was performed by 1H-NMR spectrum. The measurement results are shown as follows.

Workup

  1. temperatureunder reflux
  2. temperatureto cool
  3. customthe organic layer was separated
  4. extractionThe aqueous layer was extracted with 300 ml of hexane
  5. washwashed with water
  6. dry with materialAfter the solution was dried over magnesium sulfate
  7. distillationthe solvent was distilled off
  8. customthe obtained product was purified by column chromatography
  9. customrecrystallized with a mixed solvent of ethanol/hexane
  10. customThe measurement results

Sources & evidence

ORD record
ord-05424564bf804c4590c91f95be880266
Source dataset
uspto-grants-2010_11
Patent number
US07834204B2

Reaction notes

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