Ethanol → 4-Tetradecylpyrrole-2-carboxylic acid

HRID 1090739Notes

Reaction equation

HRID 1090739 reaction equation
[OH-].[Na+].C(O)C.[CH2:6]([C:20]1[CH:21]=[C:22]([C:25]([O:27]C)=[O:26])[NH:23][CH:24]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]>O>[CH2:6]([C:20]1[CH:21]=[C:22]([C:25]([OH:27])=[O:26])[NH:23][CH:24]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 19371041Methyl 4-tetradecylpyrrole-2-carboxylate

Product 1

HCID 150232964-Tetradecylpyrrole-2-carboxylic acidYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution (1 ml) of 2N sodium hydroxide was added to an ethanol solution (5 ml) of 0.22 g (0.69 mmol) of methyl 4-tetradecylpyrrole-2-carboxylate prepared in Example 9 and heated under reflux for 13 hours. Water was added to the resulting mixture, and then washed with ether. After acidifying the aqueous layer with hydrochloric acid, the mixture was extracted with ether and dried over anhydrous magnesium sulfate. The removal of the solvent afforded 0.19 g (95% yield) of 4-tetradecylpyrrole-2-carboxylic acid, m.p. 148°-150° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 13 hours
  3. washwashed with ether
  4. extractionthe mixture was extracted with ether
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe removal of the solvent

Sources & evidence

ORD record
ord-857c7f8cb66d4795b612d56f31b2c8a7
Source dataset
uspto-grants-1992_01
Patent number
US05082856

Reaction notes

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