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

HRID 1450032Notes

Reaction equation

HRID 1450032 reaction equation
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

Participants

7

Reactant 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

Product 1

HCID 67729115Tris(2,2,6,6-tetramethyl-benzo[1,2-d:4,5-d']bis(1,3)-dioxole-4-yl)methaneYield 88.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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 Na2S2O3 ×5 H2O 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.

Workup

  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)

Sources & evidence

ORD record
ord-dfbba12960964d80927dbd1495a8dc0c
Source dataset
uspto-grants-1997_02
Patent number
US05599522

Reaction notes

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