[C:1]1([C:7]2[O:11][C:10]([CH:12]=[O:13])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-:14].[Na+]>[N+]([O-])([O-])=O.[Ag+]>[C:1]1([C:7]2[O:11][C:10]([C:12]([OH:14])=[O:13])=[CH:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1To 5-phenyl-2-furaldehyde (35) (690 mg, 4.01 mmol) was added solid NaOH (176 mg, 4.40 mmol) then 10% NaOH solution (6.2 mL). Silver nitrate (680 mg, 4.00 mmol) was added and the reaction mixture heated to 60° C. for 4.5 hours then cooled to ambient temperature. The reaction mixture was then filtered and washed with water. The filtrate was acidified to pH 2 using 2N HCl and the precipitated product filtered and dried to give the title compound.
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