m-Chloroperbenzoic acid → HCID 11817395, compound

HRID 2079489Notes

Reaction equation

HRID 2079489 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[CH2:5][S:6][CH2:7][C:8]([OH:10])=[O:9].C1C=C(Cl)C=C(C(OO)=[O:24])C=1>C(Cl)Cl>[OH:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[CH2:5][S:6]([CH2:7][C:8]([OH:10])=[O:9])=[O:24]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 24754614HCID 24754614, compound

Product 1

HCID 11817395HCID 11817395, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-5 °C

Procedure

To a cooled (−5° C.) solution of 2-((3-hydroxy-4-methoxybenzyl)sulfanyl)acetic acid (2.9 g) in anhydrous DCM (15 mL) is added MCPBA (20 mmol, 50% concentration basis, Lancaster). The reaction mixture is stirred at −5° C. for 6 hours. The precipitated 3-chlorobenzoic acid is removed by filtration. The filtrate is washed with water, dried over magnesium sulfate and concentrated. After removal of the solvent, the product 2-((3-hydroxy-4-methoxy-benzyl)sulfinyl)acetic acid is purified either by crystallization or by silica gel chromatography.

Workup

  1. customThe precipitated 3-chlorobenzoic acid is removed by filtration
  2. washThe filtrate is washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customAfter removal of the solvent
  6. customthe product 2-((3-hydroxy-4-methoxy-benzyl)sulfinyl)acetic acid is purified either by crystallization or by silica gel chromatography

Sources & evidence

ORD record
ord-8c584f4790b04e3eb42224dae5bc067f
Source dataset
uspto-grants-2011_04
Patent number
US07932242B2

Reaction notes

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