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

HRID 1090750Notes

Reaction equation

HRID 1090750 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 15023333Methyl 4-(1-trans-tridecenyl)pyrrole-2-carboxylate

Product 1

HCID 150233314-(1-trans-Tridecenyl)pyrrole-2-carboxylic acidYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An aqueous solution (8 ml) containing 340 mg (8.0 mmol) of 95% sodium hydroxide was added to an ethanol solution (20 ml) of 1.30 g (4.3 mmol) of methyl 4-(1-trans-tridecenyl)pyrrole-2-carboxylate prepared in Example 48, 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 resulting residue was recrystallized from a mixed solution of hexane and tetrahydrofuran to give 940 mg (72% yield) of 4-(1-trans-tridecenyl)pyrrole-2-carboxylic acid, m.p. 161°-163° 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 resulting residue was recrystallized from a mixed solution of hexane and tetrahydrofuran

Sources & evidence

ORD record
ord-c8468b6855ad4714bd953f407d19dfd7
Source dataset
uspto-grants-1992_01
Patent number
US05082856

Reaction notes

Loading…