(p-Chlorophenyl)trmethylsilane → HCID 21417831, compound

HRID 441797Notes

Reaction equation

HRID 441797 reaction equation
C[Si](C)(C)C1C=CC(Cl)=CC=1.[Mg].CNC1C=CC=CC=1C=O.[CH3:23][NH:24][C:25]1[CH:42]=[CH:41][C:28]([CH:29]([OH:40])[C:30]2[CH:35]=[CH:34][C:33]([Si:36]([CH3:39])([CH3:38])[CH3:37])=[CH:32][CH:31]=2)=[CH:27][CH:26]=1>N1C=CC=CC=1.O>[CH3:23][NH:24][C:25]1[CH:26]=[CH:27][C:28]([CH:29]([OH:40])[C:30]2[CH:35]=[CH:34][C:33]([Si:36]([CH3:37])([CH3:39])[CH3:38])=[CH:32][CH:31]=2)=[CH:41][CH:42]=1.[CH3:23][NH:24][C:25]1[CH:26]=[CH:27][C:28]([C:29]([C:30]2[CH:35]=[CH:34][C:33]([Si:36]([CH3:38])([CH3:37])[CH3:39])=[CH:32][CH:31]=2)=[O:40])=[CH:41][CH:42]=1

Participants

8

Reactant 4

HCID 66351(p-Chlorophenyl)trmethylsilaneHCID 2675692-(methylamino)benzaldehydeHCID 5462224MagnesiumHCID 21417831HCID 21417831, compound

Product 2

HCID 21417831HCID 21417831, compoundHCID 21417851HCID 21417851, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1049PyridineSolvent2×

Procedure

4-Methylamino-4'-trimethylsilylbenzhydrol was prepared by a Grignard reagent formulated from 0.2 mole of 4-trimethylsilylchlorobenzene and 0.2 mole of magnesium with 0.2 mole of N-methylaminobenzaldehyde. 0.4 mole of the thus obtained 4-methylamino-4'-trimethylsilylbenzhydrol was dissolved in pyridine, and to the resultant solution was added, dropwise over a period of 40 hours at room temperature, an oxidizing agent prepared by adding 125 ml of pyridine to a solution of 7.5 ml of water and 12.5 mole of chromic anhydride under agitation while being cooled with water. The reaction product was refined by chromatography using silica gel, to obtain 41 g of 4-methylamino-4'-trimethylsilyl benzophenone in a yield of 38%.

Workup

  1. customan oxidizing agent prepared

Sources & evidence

ORD record
ord-ec764d0c43b74074811fa9878085baf4
Source dataset
uspto-grants-1977_08
Patent number
US04042613

Reaction notes

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