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

HRID 1380704Notes

Reaction equation

HRID 1380704 reaction equation
Cl[CH:2]([SiH3:4])Cl.[C:5]([C:9]1[CH:14]=[C:13]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:12]=[C:11]([C:19]2[C:20]([OH:33])=[C:21]([C:29]([CH3:32])([CH3:31])[CH3:30])[CH:22]=[C:23]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH:24]=2)[C:10]=1[OH:34])([CH3:8])([CH3:7])[CH3:6].C(N(CC)CC)C>C1(C)C=CC=CC=1>[C:15]([C:13]1[CH:14]=[C:9]([C:5]([CH3:8])([CH3:7])[CH3:6])[C:10]2[O:34][SiH:4]([CH3:2])[O:33][C:20]3[C:21]([C:29]([CH3:31])([CH3:30])[CH3:32])=[CH:22][C:23]([C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:24][C:19]=3[C:11]=2[CH:12]=1)([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 808083,3',5,5'-Tetrakis(1,1-dimethylethyl)(1,1'-biphenyl)-2,2'-diolHCID 57353436(Dichloromethyl)silane

Product 1

HCID 1233536742,4,8,10-Tetra-t-butyl-6-methyl-dibenzo[d,f][1,3,2]dioxasilepin

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

In a flame-dried flask under a dry nitrogen atmosphere, a stirred solution of 23.0 grams (0.20 mole) of dichloromethylsilane in 200 ml toluene is treated slowly with a solution of 82.1 grams (0.20 mole) of 3,3',5,5'-tetra-tert-butyl-biphenyl-2,2'-diol and 40.5 grams (0.40 mole) of triethylamine in 250 ml toluene at 5°-10° C. The reaction mixture is stirred at room temperature for 12 hours following the addition, is then filtered to remove triethylamine hydrochloride, and the solvent removed in vacuo. The residue is recrystallized from acetonitrile-toluene giving 69.4 grams (77%) of white crystals, mp 191°-198° C.

Workup

  1. additionthe addition
  2. filtrationis then filtered
  3. customto remove triethylamine hydrochloride
  4. customthe solvent removed in vacuo
  5. customThe residue is recrystallized from acetonitrile-toluene giving 69.4 grams (77%) of white crystals, mp 191°-198° C.

Sources & evidence

ORD record
ord-a283c284d678409da363ab2b5c8307c3
Source dataset
uspto-grants-1986_04
Patent number
US04582870

Reaction notes

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