Water → 4-Methoxy-dibenzofuran-1-carbaldehyde

HRID 2427853Notes

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.O>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-methoxy-dibenzofuran (3.07 g, 15.5 mmoles) is dissolved in DCM (50 mL) under nitrogen atmosphere. The solution is cooled to 0° C. and dichloromethyl-methyl ether (1.68 mL, 18.6 mmoles) and subsequently TiCl4 (1N solution in DCM, 18.6 mL, 18.6 mmoles) are added dropwise. The solution is stirred at 0° C. and the reaction is completed after 1 hour. The reaction mixture is poured into cold water and extracted with DCM. The combined organic layers are washed again with water and brine, dried over sodium sulphate and evaporated to dryness to give 3.54 g of crude compound. The reaction is repeated on additional 2.04 g of starting material to yield additional 2.51 g of crude compound. The two crude mixtures are combined and purified together by flash chromatography on SiO2 (eluent: gradient AcOEt/hexane from 10/90 to 20/80) to give 3.8 g of the desired compound.

Workup

extractionextracted with DCM
washThe combined organic layers are washed again with water and brine
dry with materialdried over sodium sulphate
customevaporated to dryness
customto give 3.54 g of crude compound
customto yield additional 2.51 g of crude compound
custompurified together by flash chromatography on SiO2 (eluent: gradient AcOEt/hexane from 10/90 to 20/80)

Sources & evidence

ORD record: ord-f62bc25366cc40819e8c4ae22980a501
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968724B2

Reaction notes

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