Carbon Dioxide → HCID 53772702, compound

HRID 1288727Notes

Reaction equation

HRID 1288727 reaction equation
C([Li])CCC.[Cl:6][C:7]1[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10].[C:19](=[O:21])=[O:20]>C1COCC1>[Cl:6][C:7]1[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:14]([Cl:18])[CH:15]=[CH:16][C:17]=1[C:19]([OH:21])=[O:20]

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 2737439ethyl 2,6-dichlorobenzoateHCID 178418339Butyllithium

Product 1

HCID 53772702HCID 53772702, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

n-Butyllithium (2.5 M in hexane, 16.5 ml) was added to a solution of ethyl 2,6-dichlorobenzoate (6.89 g) in THF while maintaining the temperature below -70° C. The mixture was stirred at -78° C. for 1 hour and poured onto solid carbon dioxide pellets. The mixture was acidified to pH1 and extracted with ether, washed with water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was recrystallized from a mixture of cyclohexane and ether to give 2,4-dichloro-3-ethoxycarbonylbenzoic acid (435 g) a s a white solid mp 168° C.

Workup

  1. temperaturewhile maintaining the temperature below -70° C
  2. extractionextracted with ether
  3. washwashed with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness
  7. customthe residue was recrystallized from a mixture of cyclohexane and ether

Sources & evidence

ORD record
ord-3146af1be07448fbae86da8efcd11f75
Source dataset
uspto-grants-1998_05
Patent number
US05747424

Reaction notes

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