Sodium Hydroxide → 4-[(4-Chlorophenyl)sulfanyl]-3-nitrobenzoic acid

HRID 1817171Notes

Reaction equation

HRID 1817171 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:19]=[CH:18][C:12]([C:13]([O:15]CC)=[O:14])=[CH:11][C:10]=2[N+:20]([O-:22])=[O:21])=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C.C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][C:9]2[CH:19]=[CH:18][C:12]([C:13]([OH:15])=[O:14])=[CH:11][C:10]=2[N+:20]([O-:22])=[O:21])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67213328HCID 67213328, compound

Product 1

HCID 7061974-[(4-Chlorophenyl)sulfanyl]-3-nitrobenzoic acidYield 100.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The above-mentioned ethyl 4-(4-chlorophenylthio)-3-nitrobenzoate (760 mg, 2.25 mmol) was dissolved in a mixture of ethanol (5 mL) and THF (10 mL). After addition of 2M aqueous sodium hydroxide (2.25 mL, 4.50 mmol), the mixture was stirred at room temperature for 4 hours and placed under reduced pressure to distill the solvent off. To the residue were added water (20 mL) and 2M aqueous hydrochloric acid until the mixture reached pH 2. The precipitated crystalline product was collected by filtration, washed successively with water (5 mL×3), a mixture (5 mL) of ethanol and water (1/4) and hexane (5 mL×2), and dried at 40° C. under reduced pressure, to obtain 703 mg (yield 100%) of the titled compound as a yellow crystalline product.

Workup

  1. distillationto distill the solvent off
  2. additionTo the residue were added water (20 mL) and 2M aqueous hydrochloric acid until the mixture
  3. filtrationThe precipitated crystalline product was collected by filtration
  4. washwashed successively with water (5 mL×3)
  5. dry with materiala mixture (5 mL) of ethanol and water (1/4) and hexane (5 mL×2), and dried at 40° C. under reduced pressure

Sources & evidence

ORD record
ord-9b4f5c7d6f6a41b4b79b3dfaf3d5720d
Source dataset
uspto-grants-2009_10
Patent number
US07598254B2

Reaction notes

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