Hydrogen Peroxide → HCID 58550716, compound

HRID 1908129Notes

Reaction equation

HRID 1908129 reaction equation
[CH:1]([S:4][C:5]1[CH:15]=[CH:14][C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:7][CH:6]=1)([CH3:3])[CH3:2].OO.C([O-])([O-])=[O:19].[Na+].[Na+]>CC(O)=O>[CH:1]([S:4]([C:5]1[CH:15]=[CH:14][C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:7][CH:6]=1)=[O:19])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 10340Sodium Carbonate2×HCID 58551422HCID 58551422, compound

Product 1

HCID 58550716HCID 58550716, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of ethyl 4-isopropylsulfanylbenzoate (350 mg, 1.6 mmol) and H2O2 (180 μL of 30% w/v, 1.6 mmol) in AcOH (2 mL) was stirred at ambient temperature for 3 h. The mixture was poured into sat. aq. Na2CO3 and the pH was adjusted to 10 with solid Na2CO3. The mixture was extracted with EtOAc (3×). The organics were combined and washed with sat. aq. Na2CO3, water (2×), then brine. The organic layer was dried over magnesium sulfate and was evaporated to dryness. The residue was purified by column chromatography (20-50% EtOAc in hexanes) to give ethyl 4-isopropylsulfinylbenzoate (65%). ESI-MS m/z calc. 240.1. found 241.3 (M+1)+. Retention time: 1.16 minutes (3 min run).

Workup

  1. extractionThe mixture was extracted with EtOAc (3×)
  2. washwashed with sat. aq. Na2CO3, water (2×)
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customwas evaporated to dryness
  5. customThe residue was purified by column chromatography (20-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-62d49e0bd47d4b1fab308773fb57b0cc
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

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