Sulfuric Acid → 4-(1-cis-Tridecenyl)pyrrole-2-carboxylic acid

HRID 1090748Notes

Reaction equation

HRID 1090748 reaction equation
[OH-].[Na+].[CH:3](/[C:16]1[CH:17]=[C:18]([C:21]([O:23]C)=[O:22])[NH:19][CH:20]=1)=[CH:4]/[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].S(=O)(=O)(O)O>C(O)C>[CH:3](/[C:16]1[CH:17]=[C:18]([C:21]([OH:23])=[O:22])[NH:19][CH:20]=1)=[CH:4]/[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 15023334Methyl 4-(1-cis tridecenyl)pyrrole-2-carboxylate

Product 1

HCID 150233324-(1-cis-Tridecenyl)pyrrole-2-carboxylic acidYield 45%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An aqueous solution (25 ml) containing 860 mg (20.4 mmol) of 95% sodium hydroxide was added to an ethanol solution (50 ml) of 3.10 g (10.2 mmol) of methyl 4-(1-cis-tridecenyl)pyrrole-2-carboxylate prepared in Example 46, and the whole was heated under reflux for 1 hour. The reaction mixture was acidified with 6N sulfuric acid and extracted with ethyl acetate. The extract was washed with an aqueous saturated solution of sodium chloride, dried over anhydrous magnesium sulfate and treated with activated carbon. After removing the solvent under reduced pressure, the residue was recrystallized from a mixed solvent of hexane and tetrahydrofuran to give 1.33 g (45% yield) of 4-(1-cis-tridecenyl)pyrrole-2-carboxylic acid, m.p. 157°-158° C.

Workup

  1. temperaturethe whole was heated
  2. temperatureunder reflux for 1 hour
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with an aqueous saturated solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. additiontreated with activated carbon
  7. customAfter removing the solvent under reduced pressure
  8. customthe residue was recrystallized from a mixed solvent of hexane and tetrahydrofuran

Sources & evidence

ORD record
ord-369e85f070b44fa68104b5633ff918a5
Source dataset
uspto-grants-1992_01
Patent number
US05082856

Reaction notes

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