Sodium Iodide → Tris(2,2,6,6-tetramethyl-benzo[1,2-d:4,5-d']bis(1,3)-dioxole-4-yl)methane

HRID 400279Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 400279
C[Si](Cl)(C)C.[I-].[Na+].[CH3:8][C:9]1([CH3:57])[O:13][C:12]2[C:14]([C:23]([C:41]3[C:51]4[O:52][C:53]([CH3:56])([CH3:55])[O:54][C:50]=4[CH:49]=[C:43]4[O:44][C:45]([CH3:48])([CH3:47])[O:46][C:42]=34)([C:25]3[C:35]4[O:36][C:37]([CH3:40])([CH3:39])[O:38][C:34]=4[CH:33]=[C:27]4[O:28][C:29]([CH3:32])([CH3:31])[O:30][C:26]=34)O)=[C:15]3[O:19][C:18]([CH3:21])([CH3:20])[O:17][C:16]3=[CH:22][C:11]=2[O:10]1.[Al].[O-]S([O-])(=S)=O.[Na+].[Na+]>C(#N)C>[CH3:39][C:37]1([CH3:40])[O:36][C:35]2[C:25]([CH:23]([C:14]3[C:12]4[O:13][C:9]([CH3:57])([CH3:8])[O:10][C:11]=4[CH:22]=[C:16]4[O:17][C:18]([CH3:21])([CH3:20])[O:19][C:15]=34)[C:41]3[C:42]4[O:46][C:45]([CH3:47])([CH3:48])[O:44][C:43]=4[CH:49]=[C:50]4[O:54][C:53]([CH3:55])([CH3:56])[O:52][C:51]=34)=[C:26]3[O:30][C:29]([CH3:31])([CH3:32])[O:28][C:27]3=[CH:33][C:34]=2[O:38]1

Komponenten

7

Edukt 5

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 24477Sodium ThiosulfateHCID 5359268AluminumHCID 10952571Tris(2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']bis(1,3)dioxole-4-yl)methanol

Produkt 1

HCID 67729115Tris(2,2,6,6-tetramethyl-benzo[1,2-d:4,5-d']bis(1,3)-dioxole-4-yl)methaneAusbeute 88,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Trimethylsilyl chloride (68.1 mL, 539 mmol) and sodium iodide (81.0 g, 540 mmol) were mixed in acetonitrile (500 mL), and tris(2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dioxole-4-yl)methanol (62.4 g, 90.2 mmol, Example 44) and was added with efficient stirring at room temperature. The reaction flask was surrounded with aluminum foil to prevent light to enter. After stirring for 24 h, the reaction mixture was poured into 2 L of a Na2S2O3 solution (70 g of Na2 S2O3 ×5H2O in 2 L of water). A yellow precipitate was formed, filtered off and was left to dry on the filter under suction (2 h). The product was triturated with i-PrOH twice, filtered and washed with cold diisopropyl ether (15 mL) to yield 54.1 g (88%) of the product tris(2,2,6,6-tetramethyl-benzo[1,2-d:4,5-d']bis(1,3)dioxole-4-yl)methane.

Aufarbeitung

  1. stirringAfter stirring for 24 h
  2. customA yellow precipitate was formed
  3. filtrationfiltered off
  4. waitwas left
  5. customto dry on the
  6. filtrationfilter under suction (2 h)
  7. customThe product was triturated with i-PrOH twice
  8. filtrationfiltered
  9. washwashed with cold diisopropyl ether (15 mL)

Quellen und Nachweise

ORD-Eintrag
ord-2bc79df057924690af2b574b9c8fd810
Quelldatensatz
uspto-grants-1998_10
Patentnummer
US05827501

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