Methyl 4-chlorobenzoate → Sodium p-chlorobenzoate

HRID 3941

Reaction equation

HRID 3941 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-].[Na+: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.[Na+:17]

Participants

4

Reactant 2

HCID 14307Methyl 4-chlorobenzoateHCID 23672319Sodium trimethylsilanolate

Product 1

HCID 23691027Sodium p-chlorobenzoateYield 94.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The procedure of Example 1 was followed using methyl 4-chlorobenzoate (4.55 g, 26.6 mmol), sodium trimethylsilanolate (2.99 g, 26.6 mmol), dry toluene (150 mL), and 4 h of heating at 80°. Sodium 4-chlorobenzoate (4.50 g, 86% yield) was isolated as a white solid: 1H NMR (D2O, DSS, 80 MHz) δ 7.65 ppm (ABq, Δν1-3 =29 Hz, J=8 Hz, Ar--H's, 4H).

Workup

  1. temperatureof heating at 80°

Sources & evidence

ORD record
ord-4e5e8dfb24b64e2785502aae5a36ffcf
Source dataset
uspto-grants-1988_02
Patent number
US04723016

Linked notes

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