4,4'-Dihydroxybiphenyl → 4,4'-Bis-(4-dimethylsilylbenzoyloxy)biphenyl

HRID 1197727Notes

Reaction equation

HRID 1197727 reaction equation
[CH3:1][SiH:2]([CH3:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1.[OH:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=2)=[CH:16][CH:15]=1>O1CCOCC1>[CH3:1][SiH:2]([CH3:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7]([O:13][C:14]2[CH:15]=[CH:16][C:17]([C:20]3[CH:25]=[CH:24][C:23]([O:26][C:7](=[O:8])[C:6]4[CH:5]=[CH:4][C:3]([SiH:2]([CH3:1])[CH3:12])=[CH:11][CH:10]=4)=[CH:22][CH:21]=3)=[CH:18][CH:19]=2)=[O:8])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 71124,4'-DihydroxybiphenylHCID 71434831p-Dimethylsilylbenzoyl chloride

Product 1

HCID 1237997974,4'-Bis-(4-dimethylsilylbenzoyloxy)biphenyl

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 49.7 g (0.250 mol) of p-dimethylsilylbenzoyl chloride and 18.6 g (0.100 mol) of 4,4'-dihydroxybiphenyl in 40 ml of dry dioxane was boiled for 15 hours. The completeness of the reaction was checked by thin-layer chromatography. After the solvent had been stripped off in vacuo on a rotary evaporator, the crude product was recrystallized from toluene, to give 4,4'-bis-(4-dimethylsilylbenzoyloxy)biphenyl, [-4 s 146 n 184 i].

Workup

  1. customAfter the solvent had been stripped off in vacuo on a rotary evaporator
  2. customthe crude product was recrystallized from toluene

Sources & evidence

ORD record
ord-dea0147276274f9f9450c59bffb3d6df
Source dataset
uspto-grants-1994_01
Patent number
US05277838

Reaction notes

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