Methyl iodide → Benzoic acid, 2,3,4,5-tetrachloro-6-cyano-, methyl ester

HRID 1111194Notes

Reaction equation

HRID 1111194 reaction equation
[K].[Cl:2][C:3]1[C:4]([C:15]#[N:16])=[C:5]([C:9]([Cl:14])=[C:10]([Cl:13])[C:11]=1[Cl:12])[C:6]([OH:8])=[O:7].[CH2:17](C(C)=O)C.CI>O>[Cl:2][C:3]1[C:4]([C:15]#[N:16])=[C:5]([C:9]([Cl:14])=[C:10]([Cl:13])[C:11]=1[Cl:12])[C:6]([O:8][CH3:17])=[O:7]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 6569Methyl Ethyl KetoneHCID 5462222PotassiumHCID 140477052,3,4,5-Tetrachloro-6-cyanobenzoic acid

Product 1

HCID 79319Benzoic acid, 2,3,4,5-tetrachloro-6-cyano-, methyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

12.9 g of the potassium salt of 3,4,5,6-tetrachloro-2-cyanobenzoic acid are heated for 20 hours under reflux in a mixture of 30 ml of water, 60 ml of methyl ethyl ketone and 11.4 g of methyl iodide. The aqueous phase is separated and the organic phase is concentrated by evaporation. Recrystallisation of the crude product (which contains only a small amount of impurities according to analysis by thin-layer chromatography) from ethanol affords 7.5 g of pure methyl 3,4,5,6-tetrachloro-2-cyanobenzoate with a melting point of 83°-84° C.

Workup

  1. customThe aqueous phase is separated
  2. concentrationthe organic phase is concentrated by evaporation
  3. customRecrystallisation of the crude product (which

Sources & evidence

ORD record
ord-69a0ccf906b7406885ef849bfa64b83c
Source dataset
uspto-grants-1990_12
Patent number
US04978768

Reaction notes

Loading…