Hydrochloric Acid → 3-(4-Mercapto-2-methyl-phenyl)-propionic Acid Methyl Ester

HRID 1785200Notes

Reaction equation

HRID 1785200 reaction equation
[CH3:1][O:2][C:3](=[O:19])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]C(=O)N(C)C)=[CH:8][C:7]=1[CH3:18].C[O-].[Na+].Cl>CO.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:19])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([SH:12])=[CH:8][C:7]=1[CH3:18]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 574319693-(4-Dimethylcarbamoylsulfanyl-2-methyl-phenyl)-propionic acid methyl ester

Product 1

HCID 541446143-(4-Mercapto-2-methyl-phenyl)-propionic Acid Methyl EsterYield 118.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-(4-Dimethylcarbamoylsulfanyl-2-methyl-phenyl)-propionic acid methyl ester (5.01 g, 17.8 mmol) is diluted with methanol (30 mL) and to this is added sodium methoxide (1.7 mL of 4M in methanol, 7.23 mmol). The reaction is heated to reflux under nitrogen and monitored by TLC. After complete conversion, 20 h., the reaction is allowed to cool to room temperature. The reaction is neutralized with 1N HCl (7.23 mL) and diluted with ethyl acetate (150 mL). The two phases are separated and the organic layer is washed with water (75 mL), then brine (75 mL). The organic layer is then dried over anhydrous sodium sulfate, then concentrated to yield 4.43 g crude product that is used without further purification.

Workup

  1. temperatureThe reaction is heated
  2. temperatureto reflux under nitrogen
  3. customAfter complete conversion, 20 h.
  4. customThe two phases are separated
  5. washthe organic layer is washed with water (75 mL)
  6. dry with materialThe organic layer is then dried over anhydrous sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f1a45547b0f44f63abaff48e45bcb3bf
Source dataset
uspto-grants-2009_03
Patent number
US07504433B2

Reaction notes

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