Selenium Dioxide → 1-(4-Methoxy-2-methylphenyl)propane-1,2-dione

HRID 69323Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](=[O:12])[CH3:11])=[C:5]([CH3:13])[CH:4]=1.[Se](=O)=[O:15]>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:15])[C:10](=[O:12])[CH3:11])=[C:5]([CH3:13])[CH:4]=1

Participants

Conditions

Temperature: 100 °C

Procedure

C8 (6.00 g, 33.7 mmol) and selenium dioxide (7.47 g, 67.3 mmol) were suspended in 1,4-dioxane (50 mL) and heated at 100° C. for 18 hours. The reaction mixture was cooled to room temperature and filtered through Celite; the filtrate was concentrated in vacuo. Silica gel chromatography (Eluent: 10% ethyl acetate in heptane) afforded the product as a bright yellow oil. Yield: 2.55 g, 13.3 mmol, 39%. LCMS m/z 193.1 [M+H+]. 1H NMR (400 MHz, CDCl3) δ 7.66 (d, J=8.6 Hz, 1H), 6.81 (br d, half of AB quartet, J=2.5 Hz, 1H), 6.78 (br dd, half of ABX pattern, J=8.7, 2.6 Hz, 1H), 3.87 (s, 3H), 2.60 (br s, 3H), 2.51 (s, 3H).

Workup

temperatureThe reaction mixture was cooled to room temperature
filtrationfiltered through Celite
concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-aa338a7367e74847b3f78a5e6e1deb11
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822494B2

Reaction notes

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