Hydrogen Peroxide → HCID 58706328, compound

HRID 1990847Notes

Reaction equation

HRID 1990847 reaction equation
[CH2:1]([S:3]([C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([O:13][CH2:14][CH3:15])[CH:12]=1)[CH:8]=[O:9])=[O:4])[CH3:2].[OH:16]O.O.[OH-].[Na+]>C(O)(=O)C>[CH2:1]([S:3]([C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([O:13][CH2:14][CH3:15])[CH:12]=1)[CH:8]=[O:9])(=[O:16])=[O:4])[CH3:2]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 14798Sodium HydroxideHCID 58706337HCID 58706337, compound

Product 1

HCID 58706328HCID 58706328, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of (±)-3-ethanesulfinyl-5-ethoxy-benzaldehyde (0.39 g, 1.72 mmol, 1.0 equiv) in conc. acetic acid (10 mL) was added a solution of 35% hydrogen peroxide in water (0.60 mL, 0.67 g, 6.89 mmol, 4.0 equiv). After stirring the reaction mixture for 18 h at rt, the pH was adjusted to 10 by addition of a 1 M solution of NaOH, extracted with ethyl acetate (3×50 mL) and the combined organic phases dried over MgSO4. The organic solvent was removed by evaporation under reduced pressure and the crude material purified with column chromatography on silica eluting with heptane/ethyl acetate (1:1) providing 0.09 g (22%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 1.31 (t, J=7.4 Hz, 3H), 1.48 (t, J=7.0 Hz, 3H), 3.17 (q, J=7.4 Hz, 2H), 4.17 (q, J=7.0 Hz, 2H), 7.63-7.66 (m, 2H), 7.94-7.95 (m, 1H), 10.04 (s, 1H). 13C NMR (75 MHz, CDCl3): δ 11.46, 18.59, 54.59, 68.89, 122.74, 123.94, 125.68, 142.60, 145.26, 164.29, 194.24. MS (ISP): 243.3 [M+H]+.

Workup

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. dry with materialthe combined organic phases dried over MgSO4
  3. customThe organic solvent was removed by evaporation under reduced pressure
  4. customthe crude material purified with column chromatography on silica eluting with heptane/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-74453b93194d4752a37cfb31d0cca430
Source dataset
uspto-grants-2010_01
Patent number
US07645753B2

Reaction notes

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