Methyl 4-chlorobenzoate → Lithium 4-chlorobenzoate

HRID 3942

Reaction equation

HRID 3942 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[CH:4][CH:3]=1.C[Si](C)(C)[O-].[Li+:17]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O-:8])=[O:7])=[CH:4][CH:3]=1.[Li+:17]

Participants

4

Reactant 2

HCID 14307Methyl 4-chlorobenzoateHCID 74821Lithium trimethylsilanolate

Product 1

HCID 19205643Lithium 4-chlorobenzoateYield 46.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The procedure of Example 1 was followed using methyl 4-chlorobenzoate (4.3 g, 25.2 mmol), lithium trimethylsilanolate (2.42 g, 25.2 mmol), and dry toluene (100 mL) and overnight heating at reflux. Lithium 4-chlorobenzoate (1.9 g, 46% yield) was isolated as a white solid: 1H NMR (D2O) δ 7.4 (ABq, Δν1-3 =31 Hz, J=9 Hz, Ar--H's, 2 H). This solid was contaminated with a small amount of lithium trimethylsilanolate.

Workup

  1. temperatureheating
  2. temperatureat reflux

Sources & evidence

ORD record
ord-6e6d66be1f8a416f914ae00c5029e6a2
Source dataset
uspto-grants-1988_02
Patent number
US04723016

Linked notes

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