Triethylamine → 2,4,8,10-Tetra-t-butyl-12H-dibenzo[d,g][1,3,2]dioxasilocin

HRID 2164357Notes

Reaction equation

HRID 2164357 reaction equation
C(=O)=O.CC(C)=O.[CH2:8]([C:24]1[CH:29]=[C:28]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH:27]=[C:26]([C:34]([CH3:37])([CH3:36])[CH3:35])[C:25]=1[OH:38])[C:9]1[CH:14]=[C:13]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:12]=[C:11]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:10]=1[OH:23].C(N(CC)CC)C.Cl[SiH2:47]Cl>O1CCCC1>[C:30]([C:28]1[CH:27]=[C:26]([C:34]([CH3:37])([CH3:36])[CH3:35])[C:25]2[O:38][SiH2:47][O:23][C:10]3[C:11]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:12][C:13]([C:15]([CH3:18])([CH3:16])[CH3:17])=[CH:14][C:9]=3[CH2:8][C:24]=2[CH:29]=1)([CH3:33])([CH3:32])[CH3:31]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 61330DichlorosilaneHCID 843912,2'-Methylenebis(4,6-di-tert-butylphenol)HCID 18522661Acetone cardice

Product 1

HCID 1023302742,4,8,10-Tetra-t-butyl-12H-dibenzo[d,g][1,3,2]dioxasilocinYield 57.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a flame-dried flask equiped with a dry ice-acetone filled Dewar condenser and a sintered glass inlet, 42.5 grams (0.1 mole) 2,2'-methylene-bis(4,6-di-t-butylphenol) and 20.2 grams (0.2 mole) triethylamine dissolved in 100 ml tetrahydrofuran are treated slowly with 11.1 grams (0.11 mole) dichlorosilane. Filtration and recrystallization from acetonitrile-toluene gave 25.9 grams (57% yield) of a white solid mp 189°-192° C. The 1H NMR spectrum is consistent with the product.

Workup

  1. filtrationFiltration and recrystallization from acetonitrile-toluene

Sources & evidence

ORD record
ord-621f060752254482a57b0d4d085faa35
Source dataset
uspto-grants-1985_03
Patent number
US04503243

Reaction notes

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