Potassium Hydroxide → HCID 18945316, compound

HRID 399828Notes

Reaction equation

HRID 399828 reaction equation
[N:1]1([C:6]2[CH:7]=[C:8]([C:16]([O:18][CH3:19])=[O:17])[CH:9]=[C:10]([CH:15]=2)[C:11]([O:13]C)=[O:12])[CH:5]=[CH:4][CH:3]=[CH:2]1.[OH-].[K+]>CO>[CH3:19][O:18][C:16]([C:8]1[CH:9]=[C:10]([CH:15]=[C:6]([N:1]2[CH:5]=[CH:4][CH:3]=[CH:2]2)[CH:7]=1)[C:11]([OH:13])=[O:12])=[O:17]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 189451711,3-Dimethyl 5-(1H-pyrrol-1-yl)-1,3-benzenedicarboxylate

Product 1

HCID 18945316HCID 18945316, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
68 °C

Procedure

A mixture of dimethyl 5-(pyrrol-1-yl)isophthalate (80.0 g) and potassium hydroxide (20.2 g) in methanol (3.1 l) was stirred for 62 hours at 68° C. After being cooled to room temperature, the solvent was evaporated in vacuo. The residue was dissolved in water and the solution was washed with ethyl acetate. The aqueous layer was acidified with hydrochloric acid (25.5 ml) and extracted with ethyl acetate. The organic layer was washed with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was triturated with diethyl ether to afford 3-methoxycarbonyl-5-(pyrrol-1-yl)benzoic acid (53.7 g).

Workup

  1. temperatureAfter being cooled to room temperature
  2. customthe solvent was evaporated in vacuo
  3. dissolutionThe residue was dissolved in water
  4. washthe solution was washed with ethyl acetate
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was evaporated in vacuo
  9. customthe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-02216f8b7d66427bb80f6494aeebc30a
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

Loading…