Methanol → Methyl 2-(4-mercaptophenyl)acetate

HRID 398655Notes

Reaction equation

HRID 398655 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[CH3:12]O>S(=O)(=O)(O)O>[CH3:12][O:10][C:9](=[O:11])[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([SH:1])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 33905114-Mercaptophenylacetic acid

Product 1

HCID 14033178Methyl 2-(4-mercaptophenyl)acetateYield 96%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

A solution of (4-mercapto-phenyl)-acetic acid (1.00 g, 5.94 mmol) in methanol (10 mL) was treated with a catalytic amount of concentrated sulfuric acid (2 drops). The reaction was heated under reflux for 2 h. At this time, the reaction mixture was concentrated in vacuo. The residue was re-dissolved in chloroform and washed with a saturated aqueous sodium bicarbonate solution. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo to afford (4-mercapto-phenyl)-acetic acid methyl ester (1.04 g, 96%) as a colorless oil: EI-HRMS m/e calcd for C9H10O2S (M+) 182.0402, found 182.0405.

Workup

  1. temperatureThe reaction was heated
  2. temperatureunder reflux for 2 h
  3. concentrationAt this time, the reaction mixture was concentrated in vacuo
  4. dissolutionThe residue was re-dissolved in chloroform
  5. washwashed with a saturated aqueous sodium bicarbonate solution
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7ca87eae25934c70979be8e86cf41574
Source dataset
uspto-grants-2003_08
Patent number
US06610846B1

Reaction notes

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