Methanol → Methyl 2-(4-mercaptophenyl)acetate

HRID 2261789Notes

Reaction equation

HRID 2261789 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.S(=O)(=O)(O)O.[CH3:17]O>>[CH3:17][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 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 33905114-Mercaptophenylacetic acid

Product 1

HCID 14033178Methyl 2-(4-mercaptophenyl)acetateYield 68%

Procedure

To an ambient temperature solution of 4-Mercaptophenylacetic acid (5.0 g, 29.72 mmol) in MeOH (250 mL) is added sulfuric acid (1.25 mL). The reaction mixture is stirred at room temperature overnight. The reaction is concentrated and the residue is partitioned between Et2O and water. The aqueous layer is extracted with Et2O and the combined organic layers are washed with brine, dried (MgSO4), filtered, concentrated, and chromatographed (0% to 30% EtOAC/Hex) to yield the title compound (3.69 g, 68%). 1H NMR (400 MHz, CDCl3) δ 7.21 (d, 2H, J=7.9 Hz), 7.12 (d, 2H, J=8.4 Hz), 3.66 (s, 3H), 3.54 (s, 2H).

Workup

  1. concentrationThe reaction is concentrated
  2. customthe residue is partitioned between Et2O and water
  3. extractionThe aqueous layer is extracted with Et2O
  4. washthe combined organic layers are washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed (0% to 30% EtOAC/Hex)

Sources & evidence

ORD record
ord-c49a70a9c38245079707f4e60513080d
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

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