Dichlorodimethylsilane → 2,4,8,10-Tetra-t-butyl-6,6-dimethyl-dibenzo[d,f][1,3,2]dioxasilepin

HRID 1380705Notes

Reaction equation

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

Participants

Reactant 3

HCID 6398Dichlorodimethylsilane

HCID 8471Triethylamine

HCID 808083,3',5,5'-Tetrakis(1,1-dimethylethyl)(1,1'-biphenyl)-2,2'-diol

Product 1

HCID 132447552,4,8,10-Tetra-t-butyl-6,6-dimethyl-dibenzo[d,f][1,3,2]dioxasilepinYield 47%

Procedure

Utilizing procedure of Example 1, this compound is prepared from 25.8 grams (0.20 mole) dichlorodimethylsilane, 82.1 grams (0.20 mole) 3,3',5,5'-tetra-tert-butyl-biphenyl-2,2'-diol and 40.5 grams (0.40 mole) of triethylamine. Recrystallization from 2-butanone gives 43.7 grams (47%) of a white powder, mp 170°-176° C.

Workup

customRecrystallization from 2-butanone

Sources & evidence

ORD record: ord-f98d8556a3764e08adbf0db5bbdde495
Source dataset: uspto-grants-1986_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04582870

Reaction notes

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