Acetic Acid → HCID 23496502, compound

HRID 1836931Notes

Reaction equation

HRID 1836931 reaction equation
[CH3:1][Si:2]([O:23]C)([O:21]C)[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([Si:15]([CH3:20])([O:18]C)[O:16]C)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.C(O)(=O)C>CCOCC>[CH3:20][Si:15]([OH:18])([OH:16])[C:12]1[CH:13]=[CH:14][C:9]([C:6]2[CH:7]=[CH:8][C:3]([Si:2]([CH3:1])([OH:21])[OH:23])=[CH:4][CH:5]=2)=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 12040566HCID 12040566, compound

Product 1

HCID 23496502HCID 23496502, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A suspension of 4,4′-bis-(methyldimethoxysilyl)biphenyl (2.4 g, 6.62 mmol) in 5 ml of ether was stirred vigorously with 3 ml of 0.5% acetic acid solution for 32 days. The white suspension was filtered and the solid was washed three times with acetone and ether. The resulting fine white solid was dried for one day under vacuum at room temperature and gave 4,4′bis-(methyldihydroxysilyl)biphenyl in 32% yield (0.65 g, 2.10 mmol). 1H NMR (DMSO-d6, δ, ppm) 7.66 (8H, s); 6.40 (4H, s); 0.19 (6H, s). 13C NMR (DMSO-d6, δ, ppm) 144.7, 139.3, 134.9, 126.6, 0.38. 29Si NMR (DMSO-d6, δ, ppm) −21.22. Anal. Calcd.; For C14H18O4Si2: C, 54.87; H, 5.92; Si, 18.33%. Found: C, 54.82; H, 5.79; Si, 18.80%.

Workup

  1. filtrationThe white suspension was filtered
  2. washthe solid was washed three times with acetone and ether
  3. customThe resulting fine white solid was dried for one day under vacuum at room temperature

Sources & evidence

ORD record
ord-8d3d7d7b85fc47548783df98a0c33492
Source dataset
uspto-grants-2004_08
Patent number
US06780471B2

Reaction notes

Loading…