4-(Dimethylamino)Benzaldehyde → [4-(Dimethylamino)phenyl][4-(trimethylsilyl)phenyl]methanone

HRID 441794Notes

Reaction equation

[CH3:1][Si:2]([CH3:11])([CH3:10])[C:3]1[CH:8]=[CH:7][C:6](Cl)=[CH:5][CH:4]=1.[Mg].[CH3:13][N:14]([CH3:23])[C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=1>>[CH3:13][N:14]([CH3:23])[C:15]1[CH:22]=[CH:21][C:18]([C:19]([C:6]2[CH:7]=[CH:8][C:3]([Si:2]([CH3:11])([CH3:10])[CH3:1])=[CH:4][CH:5]=2)=[O:20])=[CH:17][CH:16]=1

Participants

Reactant 3

HCID 74794-(Dimethylamino)Benzaldehyde

HCID 66351(p-Chlorophenyl)trmethylsilane

HCID 5462224Magnesium

Product 1

HCID 19964147[4-(Dimethylamino)phenyl][4-(trimethylsilyl)phenyl]methanone

Procedure

A Grignard reagent prepared from 0.2 mole of 4-trimethylsilylchlorobenzene and 0.2 mole of magnesium was reacted with 0.2 mole of 4-dimethylaminobenzaldehyde. The resulting reactant was subjected to oxidation by the Oppenauer method, to yield 4-dimethylamino-4'-trimethylsilyl benzophenone.

Sources & evidence

ORD record: ord-93e35cb85c0a413280d02cca1d27596a
Source dataset: uspto-grants-1977_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04042613

Reaction notes

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