Sodium Hydroxide → 3-[3-(Methylphenylsulfamoyl)phenyl]acrylic acid

HRID 226124Notes

Reaction equation

HRID 226124 reaction equation
C[O:2][C:3](=[O:23])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([S:12](=[O:22])(=[O:21])[N:13]([CH3:20])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:7]=1.[OH-].[Na+]>CO>[CH3:20][N:13]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[S:12]([C:8]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]([OH:23])=[O:2])[CH:11]=[CH:10][CH:9]=1)(=[O:21])=[O:22]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 670195883-[3-(Methylphenylsulfamoyl)phenyl]acrylic acid methyl ester

Product 1

HCID 670195313-[3-(Methylphenylsulfamoyl)phenyl]acrylic acidYield 94.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-[3-(Methylphenylsulfamoyl)phenyl]acrylic acid methyl ester (4b) (0.150 g, 0.45 mmol) was suspended in methanol (2 ml), 1 N NaOH solution (1.35 ml, 1.35 mmol) was added and the resultant solution was stirred at ambient temperature overnight. The reaction mixture was partitioned between ethyl acetate and water. The aqueous layer was acidified with 10% HCl and extracted with ethyl acetate. The organic layer was washed successively with water, saturated NaCl, and dried (Na2SO4). The solvent was removed to give the title compound (0.135 g, 94%).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed successively with water, saturated NaCl
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was removed

Sources & evidence

ORD record
ord-b79d696ecdf648d69028bd8b058d6e62
Source dataset
uspto-grants-2009_07
Patent number
US07557140B2

Reaction notes

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