Hydrogen Peroxide → HCID 58706339, compound

HRID 1990855Notes

Reaction equation

[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([O:15][CH2:16][CH3:17])[C:11]=1[S:12]([CH3:14])=[O:13])[CH:7]=[O:8])[CH3:2].[OH:18]O.O>C(O)(=O)C>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([O:15][CH2:16][CH3:17])[C:11]=1[S:12]([CH3:14])(=[O:18])=[O:13])[CH:7]=[O:8])[CH3:2]

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of (±)-3,5-diethoxy-4-methanesulfinyl-benzaldehyde (0.60 g, 2.34 mmol, 1.0 equiv) in conc. acetic acid (10 mL) was added a solution of 35% hydrogen peroxide in water (0.41 mL, 0.46 g, 4.68 mmol, 2.0 equiv) and the solution stirred for 2 h at 40° C. Periodically, every 2 hours another 2.0 equivalents of hydrogen peroxide were added to the reaction mixture to drive the reaction to completion. After 6 h the reaction mixture was 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 0.27 g (42%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 1.51 (t, J=7.0 Hz, 6H), 3.34 (s, 3H), 4.24 (q, J=7.0 Hz, 4H), 7.10 (s, 2H), 9.95 (s, 1H). 13C NMR (75 MHz, CDCl3): δ 814.39, 46.59, 66.02, 106.62, 123.29, 140.08, 158.91, 190.95. MS (ISP): 273.0 [M+H]+.

Workup

customthe reaction to completion
extractionAfter 6 h the reaction mixture was extracted with ethyl acetate (3×50 mL)
dry with materialthe combined organic phases dried over MgSO4
customThe organic solvent was removed by evaporation under reduced pressure
customthe crude material purified with column chromatography on silica eluting with heptane/ethyl acetate (1:1)

Sources & evidence

ORD record: ord-47ec84292bcd435d8a13b1e032a5d869
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07645753B2

Reaction notes

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