Potassium Hydroxide → HCID 21838083, compound

HRID 1740303Notes

Reaction equation

HRID 1740303 reaction equation
[Cl:1][C:2]1[S:3][C:4]([Cl:21])=[CH:5][C:6]=1[C:7]1[CH:8]=[C:9]([C:17]([O:19][CH3:20])=[O:18])[CH:10]=[C:11]([CH:16]=1)[C:12]([O:14]C)=[O:13].[OH-].[K+]>CO>[CH3:20][O:19][C:17]([C:9]1[CH:10]=[C:11]([CH:16]=[C:7]([C:6]2[CH:5]=[C:4]([Cl:21])[S:3][C:2]=2[Cl:1])[CH:8]=1)[C:12]([OH:14])=[O:13])=[O:18]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 21838297HCID 21838297, compound

Product 1

HCID 21838083HCID 21838083, compoundYield 87.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of dimethyl 5-(2,5-dichlorothiophen-3-yl)isophthalate (1.70 g) and potassium hydroxide (0.28 g) in methanol (50 ml) was heated to reflux for 48 hours. After being cooled to room temperature, the solvent was removed under reduced pressure. The residue was dissolved in water and was acidified with hydrochloric acid solution. The product was extracted with ethyl acetate and the organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting with a mixture of chloroform and methanol (10:1) to afford 3-methoxycarbonyl-5-(2,5-dichlorothiophen-3-yl)benzoic acid (1.43 g).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 48 hours
  3. customthe solvent was removed under reduced pressure
  4. dissolutionThe residue was dissolved in water
  5. extractionThe product was extracted with ethyl acetate
  6. washthe organic layer was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated in vacuo
  9. customThe residue was purified by column chromatography on silica gel eluting with a mixture of chloroform and methanol (10:1)

Sources & evidence

ORD record
ord-a2ec8f2878c6448babe52f402ed6c122
Source dataset
uspto-grants-1999_10
Patent number
US05968985

Reaction notes

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