Carbon Dioxide → HCID 53772702, compound

HRID 266541Notes

Reaction equation

HRID 266541 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 (2.5M 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 (4.35 g) as 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-9b8ac4aff151498ebb926ebb49065b1d
Source dataset
uspto-grants-1997_07
Patent number
US05650533

Reaction notes

Loading…