Diethyl aluminum chloride → [2-(Dimethylamino)benzyl]-diethylaluminium

HRID 898104Notes

Reaction equation

HRID 898104 reaction equation
[Cl-].[CH2:2]([Al+:4][CH2:5][CH3:6])[CH3:3].[CH3:7][N:8]([CH3:17])[C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1[CH2:11][Li]>C1(C)C=CC=CC=1>[CH3:7][N:8]([CH3:17])[C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1[CH2:11][Al:4]([CH2:5][CH3:6])[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 16686102Diethyl aluminum chlorideHCID 178506851HCID 178506851, compound

Product 1

HCID 18622320[2-(Dimethylamino)benzyl]-diethylaluminiumYield 62%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

7.17 g (7.5 ml; 59.5 mmol) of diethylaluminium chloride were added dropwise to a suspension, cooled to −30° C., of 8.40 g (59.5 mmol) of 2-dimethylaminobenzyllithium in 150 ml of toluene in an inert nitrogen atmosphere. After slow warming to room temperature, the mixture was stirred for 15 hours in order to complete the reaction. Filtration through a D4 frit and removal of the solvent by distillation gave 8:05 g of [2-(dimethylamino)benzyl]-diethylaluminium (36.7 mmol/62%) as a colourless liquid by slow fractional distillation from the residue.

Workup

  1. customthe reaction
  2. filtrationFiltration
  3. customthrough a D4 frit and removal of the solvent
  4. distillationby distillation

Sources & evidence

ORD record
ord-14dd28a1d06a4e529c6798f2863cf3f4
Source dataset
uspto-grants-2008_04
Patent number
US07351678B2

Reaction notes

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