2-Hydroxy-1,2-bis(3-methoxyphenyl)ethanone → 1,2-Ethanedione, 1,2-bis(3-methoxyphenyl)-

HRID 2205128Notes

Reaction equation

[OH:1][CH:2]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=1)[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[CH:6]=1)=[O:4]>CC(O)=O.CC([O-])=O.CC([O-])=O.[Cu+2].O>[CH3:20][O:19][C:15]1[CH:14]=[C:13]([C:2](=[O:1])[C:3]([C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[CH:6]=2)=[O:4])[CH:18]=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 2-hydroxy-1,2-bis(3-methoxyphenyl)ethanone (3.5 g, 12.87 mmol, 1.00 equiv), NH4NO3 (1.04 g, 13.00 mmol, 1.00 equiv), and Cu(OAc)2.H2O (260 mg, 1.30 mmol, 0.10 equiv) in 80% aqueous HOAc (30 mL) was allowed to react, with stirring, for 2 hrs while the temperature was maintained at reflux in an oil bath. Upon cooling to 0° C., the solid was filtered and washed with H2O (3×30 ml), affording 2.5 g (72%) of 1,2-bis(3-methoxyphenyl)-1,2-ethandione as a yellow solid.

Workup

customto react
temperaturewas maintained
temperatureat reflux in an oil bath
filtrationthe solid was filtered
washwashed with H2O (3×30 ml)

Sources & evidence

ORD record: ord-e8d0d8ed78314b6f94b602379c3f82ef
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09370522B2

Reaction notes

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