Acetic Acid → Bicyclo[2.2.2]octane-2,3-dione

HRID 1888882Notes

Reaction equation

HRID 1888882 reaction equation
[CH:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][C:2]2=[O:9].C(O)(=[O:12])C>>[CH:4]12[CH2:7][CH2:8][CH:1]([CH2:6][CH2:5]1)[C:2](=[O:9])[C:3]2=[O:12]

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 137688Bicyclo(2.2.2)octan-2-one

Product 1

HCID 548936Bicyclo[2.2.2]octane-2,3-dione

Procedure

In analogy to Example 1 Step B]: from bicyclo[2.2.2]octan-2-one, 1.416 g, (synthesis: JOC., 1993, 58, 7622), SeO2 (2.218 g) in acetic acid (8 ml) on heating at 130° C. for 12 h, purification of the crude product by flash chromatography (heptane/AcOEt 100-75%), there was obtained bicyclo[2.2.2]octane-2,3-dione (0.396 g) as yellow solid. MS (ESI): 156 (M+NH4)+.

Workup

  1. custompurification of the crude product by flash chromatography (heptane/AcOEt 100-75%)

Sources & evidence

ORD record
ord-199435193ae1476cb6a7850f39f55f90
Source dataset
uspto-grants-2013_08
Patent number
US08501940B2

Reaction notes

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