Methane, dichloromethoxy- → 4-Methoxy-dibenzofuran-1-carbaldehyde

HRID 2383972Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:8]2[O:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:7]=2[CH:6]=[CH:5][CH:4]=1.Cl[CH:17]([O:19]C)Cl>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[C:8]2[O:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:7]=2[C:6]([CH:17]=[O:19])=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 0 °C

Procedure

4-Methoxydibenzofuran (25 g, 0.12 mol) was dissolved in DCM (300 ml) at room temperature and cooled to 0° C. To this solution TiCl4 (22.2 ml, 0.20 mol) was added drop wise at 0-2° C. The reaction mass was allowed to stir for 10 min and to that solution dichloromethyl methylether (9.7 ml, 0.107 mol) was added drop wise at 0° C. The reaction mass was stirred for 10 min and the reaction was monitored by TLC. Once the reaction was completed, the reaction mass was quenched with water and the organic layer was washed with NaHCO3 solution and brine. The organic layer was dried with sodium sulfate and concentrated under vacuum. 4-methoxy-dibenzofuran-1-carbaldehyde was isolated by column chromatography obtaining a white solid. Yield 13.5 g (48%)

Workup

additionwas added drop wise at 0° C
customthe reaction mass was quenched with water
washthe organic layer was washed with NaHCO3 solution and brine
dry with materialThe organic layer was dried with sodium sulfate
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-482ced797f614193a79b54d0e4b82755
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263648B2

Reaction notes

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