Carbon Dioxide → 3-Cyano-2,4-dichlorobenzoic acid

HRID 342984

Reaction equation

HRID 342984 reaction equation
C([N-]C(C)C)(C)C.[Li+].[Cl:9][C:10]1[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[C:11]=1[C:12]#[N:13].[C:19](=[O:21])=[O:20].O>C1COCC1.CCOCC>[C:12]([C:11]1[C:14]([Cl:18])=[C:15]([CH:16]=[CH:17][C:10]=1[Cl:9])[C:19]([OH:21])=[O:20])#[N:13]

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 962WaterHCID 3031DichlobenilHCID 2724682Lithium diisopropylamide

Product 1

HCID 540731813-Cyano-2,4-dichlorobenzoic acid

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium di-isopropylamide (2M in heptane, 25 ml) was added to a solution of 2,6-dichlorobenzonitrile (8.6 g) in THF while maintaining the temperature below -70° C. The mixture was stirred for 1.5 hours then poured onto solid carbon dioxide. It was stirred for 1 hour then diluted with ether. Water was added and the mixture was acidified to pH1. It was extracted with ether, washed with water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness to give 3-cyano-2,4-dichlorobenzoic acid (9.4 g) as a white solid mp 230°-232° C.

Workup

  1. temperaturewhile maintaining the temperature below -70° C
  2. stirringIt was stirred for 1 hour
  3. extractionIt was extracted with ether
  4. washwashed with water
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-c92932fa4ed3427f805ed3fe020bc414
Source dataset
uspto-grants-1999_01
Patent number
US05859283

Linked notes

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