Sodium Hydroxide → 4-(2-Mercaptoethyl)-1,3-benzenedicarboxylic acid

HRID 1352813Notes

Reaction equation

HRID 1352813 reaction equation
C([S:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([O:15]C)=[O:14])=[CH:9][C:8]=1[C:17]([O:19]C)=[O:18])(=O)C.[OH-].[Na+]>C1COCC1.O>[SH:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([OH:15])=[O:14])=[CH:9][C:8]=1[C:17]([OH:19])=[O:18]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 12017548Dimethyl 4-[2-(acetylthio)ethyl]-1,3-benzenedicarboxylate

Product 1

HCID 101307574-(2-Mercaptoethyl)-1,3-benzenedicarboxylic acidYield 45.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a degassed solution of dimethyl 4-[2-(acetylthio) ethyl]-1,3-benzenedicarboxylate (0.130 g, 0.44 mmol) in THF (5 mL) was added a degassed solution of 5 N NaOH (5 mL). The reaction mixture was stirred under nitrogen overnight. The reaction mixture was diluted with H2O (10 mL) and extracted with EtOAC (10 mL). The organic layer was dried over MgSO4 and concentrated to give 0.045 g of white solid (45% yield): 1H NMR (DMSO) δ 2.67 (t, 2H) 3.21 (t, 2H), 7.37 (d, 1H), 7.98 (d, 1H), 8.46 (s, 1H). 13C NMR (DMSO) δ 26.64, 40.60, 130.87, 132.05, 133.46, 133.81, 134.13, 148.53, 169.22, 170.20. Elemental analysis calculated for C10H10SO4: C, 53.09; H, 4.45; S, 14.47. Found: C, 53.37; H, 4.87; S, 12.84. MS(FAB): 225.

Workup

  1. extractionextracted with EtOAC (10 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-df784e4864a543f4894da5e4c5ead73c
Source dataset
uspto-grants-2007_05
Patent number
US07220780B2

Reaction notes

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