Sodium Hydroxide → 1-Tetradecylpyrrole-3-carboxylic acid

HRID 1090753Notes

Reaction equation

HRID 1090753 reaction equation
[OH-].[Na+].[CH2:3]([N:17]1[CH:21]=[CH:20][C:19]([C:22]([O:24]CC)=[O:23])=[CH:18]1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]>C(O)C.O>[CH2:3]([N:17]1[CH:21]=[CH:20][C:19]([C:22]([OH:24])=[O:23])=[CH:18]1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 15023354Ethyl 1-tetradecylpyrrole-3-carboxylate

Product 1

HCID 150233531-Tetradecylpyrrole-3-carboxylic acidYield 79.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2.58 g (61.3 mmol) of 95% sodium hydroxide in 100 ml of ethanol and 40 ml of water was added 5.43 g (15.3 mmol) of ethyl 1-tetradecylpyrrole-3-carboxylate obtained in Example 56. After the mixture was heated under reflux for 5 hours, the ethanol was removed under reduced pressure and 100 ml of water was added thereto. Then the mixture was acidified with concentrated hydrochloric acid to precipitate crystals, which were extracted with 70 ml and with 50 ml of ethyl acetate. The extract was washed with an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate. After removing the solvent under reduced pressure, the remaining crystals were recrystallized from hexane to give 3.76 g (79.9% yield) of 1-tetradecylpyrrole-3-carboxylic acid as white crystals, m.p. 66°-67° C.

Workup

  1. temperatureAfter the mixture was heated
  2. temperatureunder reflux for 5 hours
  3. customthe ethanol was removed under reduced pressure and 100 ml of water
  4. additionwas added
  5. customto precipitate crystals, which
  6. extractionwere extracted with 70 ml and with 50 ml of ethyl acetate
  7. washThe extract was washed with an aqueous saturated sodium chloride solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customAfter removing the solvent under reduced pressure
  10. customthe remaining crystals were recrystallized from hexane

Sources & evidence

ORD record
ord-b3ed331b50c84887a9cf9d3081512ded
Source dataset
uspto-grants-1992_01
Patent number
US05082856

Reaction notes

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