Sodium Hydroxide → 3-(4-Carboxymethylsulfanylphenoxymethyl)thiophene-2-carboxylic acid

HRID 389028Notes

Reaction equation

HRID 389028 reaction equation
[OH-].[Na+].C([O:5][C:6]([CH2:8][S:9][C:10]1[CH:26]=[CH:25][C:13]([O:14][CH2:15][C:16]2[CH:20]=[CH:19][S:18][C:17]=2[C:21]([O:23]C)=[O:22])=[CH:12][CH:11]=1)=[O:7])C>CO>[C:6]([CH2:8][S:9][C:10]1[CH:26]=[CH:25][C:13]([O:14][CH2:15][C:16]2[CH:20]=[CH:19][S:18][C:17]=2[C:21]([OH:23])=[O:22])=[CH:12][CH:11]=1)([OH:7])=[O:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68571726Methyl 3-(4-ethoxycarbonylmethylsulfanylphenoxymethyl)thiophene-2-carboxylate

Product 1

HCID 684864633-(4-Carboxymethylsulfanylphenoxymethyl)thiophene-2-carboxylic acidYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

An aqueous sodium hydroxide (19.2 g, 480 mmol) solution was added to a methanol (250 mL) solution of the compound obtained in Example 19 (35.1 g, 96 mmol), and the mixture was refluxed while heating for 2 hours. After allowing the mixture to cool in the air, the solvents were distilled off under a reduced pressure, and water was added to the residue. The solution was neutralized with hydrochloric acid, and the precipitated crystals were separated by filtration and dried, to give 30.0 g (97%) of the captioned compound.

Workup

  1. temperaturethe mixture was refluxed
  2. temperaturewhile heating for 2 hours
  3. temperatureto cool in the air
  4. distillationthe solvents were distilled off under a reduced pressure, and water
  5. additionwas added to the residue
  6. customthe precipitated crystals were separated by filtration
  7. customdried

Sources & evidence

ORD record
ord-7250f3136db143cfa194c917fa6c84fe
Source dataset
uspto-grants-2013_02
Patent number
US08377967B2

Reaction notes

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