Sodium Hydroxide → 8-Oxatricyclo(7.4.0.0,2,7)trideca-1(9),2(7),3,5,10,12-hexaene-4-carboxylic acid

HRID 659102Notes

Reaction equation

[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH:14]=[O:15].[OH-:16].[Na+]>[N+]([O-])([O-])=O.[Ag+]>[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1[C:14]([OH:16])=[O:15]

Participants

Conditions

Temperature: 60 °C

Procedure

To dibenzofuran-2-carboxaldehyde (17) (200 mg, 1.02 mmol) was added solid NaOH (49 mg, 1.22 mmol) then 10% NaOH solution (1.8 mL). Silver nitrate (173 mg, 1.02 mmol) was then added, the reaction mixture heated to 60° C. for 1.5 hours and then stirred overnight at ambient temperature. The reaction mixture was then filtered and washed with water. The filtrate was acidified to pH 2 using concentrated HCl and the precipitated product filtered and dried to give the title compound as an off-white solid. Yield: 83 mg, 38%; LC-MS tr 1.31 min; HPLC Purity: 100%; MS (ES+) m/z not detectable (M+H)

Workup

filtrationThe reaction mixture was then filtered
washwashed with water
filtrationthe precipitated product filtered
customdried

Sources & evidence

ORD record: ord-aa252529c39c4d28956351c9a99b75c6
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08080567B2

Reaction notes

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