Ethanol → HCID 9903805, compound

HRID 129343Notes

Reaction equation

HRID 129343 reaction equation
[CH2:1]([C:13]1[CH:14]=[C:15]([C:18]([O:20]C)=[O:19])[NH:16][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C(O)C.[OH-].[Na+].S(=O)(=O)(O)O>O>[CH2:1]([C:13]1[CH:14]=[C:15]([C:18]([OH:20])=[O:19])[NH:16][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

6

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 15023271HCID 15023271, compound

Product 1

HCID 9903805HCID 9903805, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
45 °C

Procedure

To 112.0 g (0.38 mol) of methyl 4-dodecylpyrrole-2-carboxylate prepared in Example 35 were added 1.45 liters of ethanol, 1.45 liters of water and 31.0 g (0.74 mol) of 95% sodium hydroxide, and the whole was heated under reflux for 2 hours. At 80° C., 1.45 liters of hot water was added and, at the same temperature, 6N sulfuric acid was added gradually to adjust the reaction solution to pH 2. After cooling the mixture to 45° C., precipitated crystals were filtered and washed with water. The crystals were dissolved in 4 liters of tetrahydrofuran, and the solution was washed twice with 1 liter of a saturated solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give crystals, which were then recrystallized from a mixed solvent 600 ml of tetrahydrofurn and 600 ml of hexane to obtain 92.6 g (87% yield) of 4-dodecylpyrrole- 2-carboxylic acid as white crystals, m.p. 152°-153° C.

Workup

  1. temperaturethe whole was heated
  2. temperatureunder reflux for 2 hours
  3. additionwas added gradually
  4. customprecipitated crystals
  5. filtrationwere filtered
  6. washwashed with water
  7. dissolutionThe crystals were dissolved in 4 liters of tetrahydrofuran
  8. washthe solution was washed twice with 1 liter of a saturated solution of sodium chloride
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customThe solvent was removed under reduced pressure
  11. customto give crystals, which
  12. customwere then recrystallized from a mixed solvent 600 ml of tetrahydrofurn and 600 ml of hexane

Sources & evidence

ORD record
ord-35342d20fc044f9fbe0f8491836aa863
Source dataset
uspto-grants-1995_11
Patent number
USRE035096

Reaction notes

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