Sodium Hydroxide → HCID 13179847, compound

HRID 1702191Notes

Reaction equation

HRID 1702191 reaction equation
[CH3:1][N:2]1[C:6]([C:7]([O:9]C)=[O:8])=[CH:5][C:4]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=2)=[C:3]1[C:20]([O:22]C)=[O:21].[OH-].[Na+]>CO.O>[CH3:1][N:2]1[C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=2)=[C:3]1[C:20]([OH:22])=[O:21]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 13179846HCID 13179846, compound

Product 1

HCID 13179847HCID 13179847, compoundYield 92.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
75 °C

Procedure

To a stirred suspension of dimethyl 1-methyl-3-[(m-methylphenoxy)methyl]pyrrole-2,5-dicarboxylate (0.32 g, 0.001 m) in a mixture of methanol (10 ml) and water (6 ml), ice cooling, was added under a nitrogen atmosphere 2.5 N sodium hydroxide solution (1.2 ml). The mixture was allowed to come to room temperature, and then set in an oil-bath at 50° C., the temperature of the bath raised to 75° C., and kept at this temperature for ca. one hour. After stirring overnight at ambient temperature, water (55 ml) was added over 5 minutes, the mixture filtered, the volume of the filtrate adjusted to 100 ml with water, and the stirred filtrate acidified dropwise with 2 ml of 2 N hydrochloride acid. After aging for 20 minutes, the mixture was filtered, the precipitate washed with water and dried to give 0.27 g (90%) of 1-methyl-3-[(m-methylphenoxy)methyl]-pyrrole-2,5-dicarboxylic acid.

Workup

  1. customto come to room temperature
  2. customset in an oil-bath at 50° C.
  3. filtrationthe mixture filtered
  4. waitAfter aging for 20 minutes
  5. filtrationthe mixture was filtered
  6. washthe precipitate washed with water
  7. customdried

Sources & evidence

ORD record
ord-92ba58154949451ea11dfc7597891dba
Source dataset
uspto-grants-1983_04
Patent number
US04380645

Reaction notes

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