Dichlorodiphenylsilane → 2,4,8,10-Tetra-tert-butyl-6,6-diphenyl-dibenzo[d,g][1,3,6,2]dioxathiasilocin

HRID 867391Notes

Reaction equation

Cl[Si:2](Cl)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[S:16]([C:32]1[CH:37]=[C:36]([C:38]([CH3:41])([CH3:40])[CH3:39])[CH:35]=[C:34]([C:42]([CH3:45])([CH3:44])[CH3:43])[C:33]=1[OH:46])[C:17]1[CH:22]=[C:21]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH:20]=[C:19]([C:27]([CH3:30])([CH3:29])[CH3:28])[C:18]=1[OH:31].C(N(CC)CC)C>C1(C)C=CC=CC=1>[C:38]([C:36]1[CH:35]=[C:34]([C:42]([CH3:45])([CH3:44])[CH3:43])[C:33]2[O:46][Si:2]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)([C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)[O:31][C:18]3[C:19]([C:27]([CH3:29])([CH3:28])[CH3:30])=[CH:20][C:21]([C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:22][C:17]=3[S:16][C:32]=2[CH:37]=1)([CH3:41])([CH3:40])[CH3:39]

Participants

Conditions

Temperature: 92 °C

Procedure

A solution of 12.66 grams of dichlorodiphenylsilane in 50 ml of toluene at 5°-10° C. is added dropwise to a solution of 22.14 grams of 2,2'-thiobis(4,6-di-tert-butylphenol) and 10.12 grams of triethylamine in 100 ml of toluene. The reaction mixture is heated at 92° C. until the reaction is complete as evidenced by the disappearance of the phenolic absorption in the IR spectrum. The triethylamine hydrochloride is removed by filtration and the solvent is removed in vacuo. The residue is recrystallized from 2-butanone to give 13.49 grams (43%) of a white solid: mp 202°-205° C.

Workup

customas evidenced by the disappearance of the phenolic absorption in the IR spectrum
customThe triethylamine hydrochloride is removed by filtration
customthe solvent is removed in vacuo
customThe residue is recrystallized from 2-butanone

Sources & evidence

ORD record: ord-c0c2774e1bd34ab18cd78baa8dbd464c
Source dataset: uspto-grants-1988_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04775497

Reaction notes

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