Water → 4-Chloro-3-cyanobenzoic acid

HRID 2414321Notes

Reaction equation

HRID 2414321 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[CH:4][C:3]=1[C:12]#[N:13].O.[OH-].[Li+].O>O1CCCC1>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[C:12]#[N:13]

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 22644672Methyl 4-chloro-3-cyanobenzoate

Product 1

HCID 226446124-Chloro-3-cyanobenzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the product from step (i) (1.5 g) and lithium hydroxide hydrate (0.84 g) in a mixture of (1:1)water and tetrahydrofuran (40 ml) was stirred at room temperature for 2 h. The tetrahydrofuran was removed under reduced pressure and the residue partitioned between diethyl ether and water. The aqueous layer was acidified with 2M hydrochloric acid then extracted with ethyl acetate. The organic layer was dried and evaporated under reduced pressure. Yield 1.3 g.

Workup

  1. customThe tetrahydrofuran was removed under reduced pressure
  2. customthe residue partitioned between diethyl ether and water
  3. extractionthen extracted with ethyl acetate
  4. customThe organic layer was dried
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-f9ddecf90deb4e12983faabd7b5a10a3
Source dataset
uspto-grants-2004_11
Patent number
US06812226B2

Reaction notes

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