Lithium Hydroxide → 4,5-Bis(3-chlorophenyl)furan-2-carboxylic acid

HRID 2190128Notes

Reaction equation

HRID 2190128 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([C:20]([O:22]CC)=[O:21])[O:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=2)[CH:5]=[CH:6][CH:7]=1.[OH-].[Li+]>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([C:20]([OH:22])=[O:21])[O:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 58064774Ethyl 4,5-bis(3-chlorophenyl)furan-2-carboxylate

Product 1

HCID 580647634,5-Bis(3-chlorophenyl)furan-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

760 mg (2.10 mmol) of the compound from Example 14A are provided in 20 ml of dioxane, and 20 ml of a 2N aqueous lithium hydroxide solution are added at room temperature. The mixture is stirred at 50° C. for two hours and subsequently concentrated. A 1N aqueous HCl solution is then added until an acidic pH is established, the mixture is extracted with dichloromethane and the organic phase is dried over magnesium sulfate, filtered and concentrated. 401 mg (57% of theory) of the title compound are obtained.

Workup

  1. concentrationsubsequently concentrated
  2. additionA 1N aqueous HCl solution is then added until an acidic pH
  3. extractionthe mixture is extracted with dichloromethane
  4. dry with materialthe organic phase is dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-75e573ea498546cdbafe8f6b5f8f2549
Source dataset
uspto-grants-2012_12
Patent number
US08324268B2

Reaction notes

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