Hydrochloric Acid → 4,4'-(Cyclopenta-2,4-dien-1-ylidenemethylene)bis(methylbenzene)

HRID 746977Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 746977
[CH3:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)=O)=[CH:4][CH:3]=1.O1CCCC1.[CH:22]1([Na])[CH:26]=[CH:25][CH:24]=[CH:23]1.Cl>O.C(OCC)C>[C:11]1([CH3:14])[CH:12]=[CH:13][C:8]([C:6]([C:5]2[CH:15]=[CH:16][C:2]([CH3:1])=[CH:3][CH:4]=2)=[C:25]2[CH:24]=[CH:23][CH:22]=[CH:26]2)=[CH:9][CH:10]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2×HCID 691484,4'-DimethylbenzophenoneHCID 178507085HCID 178507085, Verbindung

Produkt 1

HCID 124276304,4'-(Cyclopenta-2,4-dien-1-ylidenemethylene)bis(methylbenzene)Ausbeute 74,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A 200 ml two-necked flask equipped with a dropping funnel, a magnetic stirrer and a three-way cock, was purged thoroughly with nitrogen. Into the flask, 4,4′-dimethylbenzophenone 6.72 g (31.9 mmol) was introduced, and dehydrated tetrahydrofuran 30 ml was further added. With cooling in an ice bath, 2 mol/L tetrahydrofuran solution of cyclopentadienyl sodium, 19.0 ml (38.0 mmol), was dropwise added to the flask. The contents were stirred at room temperature in a nitrogen atmosphere for 6 days to obtain a solution. With the flask cooled in an ice bath, 1 N hydrochloric acid aqueous solution 100 ml and diethyl ether 100 ml were gradually added in this order. The resulting two-phase solution was poured into a 300 ml separation funnel, and the funnel was shaken several times so that the water phase was removed. The obtained organic phase was washed twice with water 100 ml and once with a saturated salt solution 100 ml, and dried over anhydrous magnesium sulfate. The solution was filtered to remove solids, and the solvent of the filtrate was distilled away to obtain a red oily matter 9.40 g. The oily matter was subjected to silica gel chromatography to obtain 6.15 g of 6,6-di-p-tolyl fulvene as a red solid (23.8 mmol, 74.5% yield). Identification of the 6,6-di-p-tolyl fulvene was made by 1H NMR, the results being given below:

Aufarbeitung

  1. customA 200 ml two-necked flask equipped with a dropping funnel, a magnetic stirrer
  2. customa three-way cock, was purged thoroughly with nitrogen
  3. temperatureWith cooling in an ice bath
  4. customto obtain a solution
  5. temperatureWith the flask cooled in an ice bath
  6. additionThe resulting two-phase solution was poured into a 300 ml separation funnel
  7. customwas removed
  8. washThe obtained organic phase was washed twice with water 100 ml and once with a saturated salt solution 100 ml
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationThe solution was filtered
  11. customto remove solids
  12. distillationthe solvent of the filtrate was distilled away
  13. customto obtain a red oily matter 9.40 g

Quellen und Nachweise

ORD-Eintrag
ord-c9e334f2460042399e68e756720a0f93
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07393965B2

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