Triethylamine → 2,4,8,10-Tetra-t-butyl-6-methyl-dibenzo[d,g][1,3,2,6]dioxasilathiocin

HRID 2164355Notes

Reaction equation

HRID 2164355 reaction equation
Cl[CH:2]([SiH3:4])Cl.[S:5]([C:21]1[CH:26]=[C:25]([C:27]([CH3:30])([CH3:29])[CH3:28])[CH:24]=[C:23]([C:31]([CH3:34])([CH3:33])[CH3:32])[C:22]=1[OH:35])[C:6]1[CH:11]=[C:10]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH:9]=[C:8]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:7]=1[OH:20].C(N(CC)CC)C>>[C:27]([C:25]1[CH:24]=[C:23]([C:31]([CH3:34])([CH3:33])[CH3:32])[C:22]2[O:35][SiH:4]([CH3:2])[O:20][C:7]3[C:8]([C:16]([CH3:18])([CH3:17])[CH3:19])=[CH:9][C:10]([C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:11][C:6]=3[S:5][C:21]=2[CH:26]=1)([CH3:30])([CH3:29])[CH3:28]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 108984374,4',6,6'-Di-tert-butyl-2,2'-thiobisphenolHCID 57353436(Dichloromethyl)silane

Product 1

HCID 1233910602,4,8,10-Tetra-t-butyl-6-methyl-dibenzo[d,g][1,3,2,6]dioxasilathiocinYield 48.7%

Procedure

Utilizing the procedure of Example 1, this compound is prepared from 5.7 grams (0.05 mole) dichloromethylsilane, 22.1 grams (0.05 mole) 2,2'-thiobis(4,6-di-t-butylphenol), and 10.1 grams (0.10 mole) triethylamine. Recrystallization twice from acetone-toluene gives 11.8 grams (48% yield) of white crystals, mp 178°-180° C.

Workup

  1. customRecrystallization twice from acetone-toluene

Sources & evidence

ORD record
ord-9e4a1e223cc543a3837e3221e3d39df1
Source dataset
uspto-grants-1985_03
Patent number
US04503243

Reaction notes

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