Sodium Hydroxide → HCID 22600906, compound

HRID 2308160Notes

Reaction equation

HRID 2308160 reaction equation
[CH2:1]([O:11][C:12]1[C:16]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[C:15]([C:28]([O:30]CC)=[O:29])[NH:14][C:13]=1[C:33]([O:35]CC)=[O:34])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[OH-].[Na+]>C(O)C>[CH2:1]([O:11][C:12]1[C:16]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[C:15]([C:28]([OH:30])=[O:29])[NH:14][C:13]=1[C:33]([OH:35])=[O:34])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22600912HCID 22600912, compound

Product 1

HCID 22600906HCID 22600906, compoundYield 65.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Into a 3-L three-necked flask, 68.6 g (131 mmoles) of the diethyl 3,4-didecyloxypyrrole-2,5-dicarboxylate and 680 ml of ethanol were put, and an aqueous sodium hydroxide solution (prepared by dissolving 52.4 g of sodium hydroxide in 655 ml of water) was dropwise added thereto over a period of 15 minutes with stirring at room temperature. Thereafter, the mixture was heated and stirred at about 60° C. for 6.5 hours. After the reaction was completed, the reaction product was cooled to room temperature, and the sodium carboxylate thus deposited was collected by filtration, followed by washing with ethanol. The resultant crystals were dispersed in a solution of a mixture of 3L of ethyl acetate and 350 ml of water, and 91 ml of 3N-hydrochloric acid was added to adjust the pH to about 1. The organic layer formed was washed with water and dried with Glauber's salt. Thereafter, the solvent was evaporated to dryness. The residue formed was recrystallized with an ethyl acetate/hexane mixed solvent to obtain 40.3 g of white crystals of 3,4-didecyloxypyrrole-2,5-dicarboxylic acid (yield: 65.8%).

Workup

  1. temperatureThereafter, the mixture was heated
  2. stirringstirred at about 60° C. for 6.5 hours
  3. temperaturethe reaction product was cooled to room temperature
  4. filtrationthe sodium carboxylate thus deposited was collected by filtration
  5. washby washing with ethanol
  6. additionThe resultant crystals were dispersed in a solution of a mixture of 3L of ethyl acetate and 350 ml of water, and 91 ml of 3N-hydrochloric acid
  7. additionwas added
  8. customThe organic layer formed
  9. washwas washed with water
  10. dry with materialdried with Glauber's salt
  11. customThereafter, the solvent was evaporated to dryness
  12. customThe residue formed
  13. customwas recrystallized with an ethyl acetate/hexane mixed solvent

Sources & evidence

ORD record
ord-8e66986b08674231bb7e7b81b798a7e0
Source dataset
uspto-grants-2004_12
Patent number
US06835471B2

Reaction notes

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