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

HRID 129345Notes

Reaction equation

HRID 129345 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-49b4de00d32349648a71873b3e2b7b6f
Source dataset
uspto-grants-1995_11
Patent number
USRE035096

Reaction notes

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