Water → 2-(3-Formyl-4-methoxybenzyl)-3-methyl-4-hydroxy-5-propyl-benzofuran

HRID 1607242Notes

Reaction equation

[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][O:6][C:7]1[CH:27]=[CH:26][C:10]([CH2:11][C:12]2[O:13][C:14]3[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH3:24])=[C:18]([OH:25])[C:15]=3[C:16]=2[CH3:17])=[CH:9][CH:8]=1.Cl[CH:29]([O:31]C)Cl.O>ClCCl>[CH:29]([C:27]1[CH:26]=[C:10]([CH:9]=[CH:8][C:7]=1[O:6][CH3:5])[CH2:11][C:12]1[O:13][C:14]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH3:24])=[C:18]([OH:25])[C:15]=2[C:16]=1[CH3:17])=[O:31]

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of aluminium chloride (214 mg; 1.6mmole) in dichloromethane (5 mL) cooled at 0° C. was added 2-(p-methoxy benzyl)-3-methyl-4-hydroxy-5-propyl benzofuran (100 mg; 0.32mmoles). A red solution resulted. To this solution was added dropwise dichloromethylmethylether (87 (1; 0.96 mmole). There was a vigorous reaction and a color change from red to green was observed. Ice and water was then added and the mixture was extracted with ethylacetate. The organic phase was dried (Na2SO4), and concentrated in vacuo and the residue was chromatographed on silica gel. Elution with 10% ethylacetate in hexane yielded 40 mg (37%) of 2-(3 formyl-4-methoxybenzyl)-3-methyl-4-hydroxy-5-propyl-benzofuran.

Workup

customA red solution resulted
customa vigorous reaction
extractionthe mixture was extracted with ethylacetate
dry with materialThe organic phase was dried (Na2SO4)
concentrationconcentrated in vacuo
customthe residue was chromatographed on silica gel
washElution with 10% ethylacetate in hexane

Sources & evidence

ORD record: ord-1fe1bb83fd534b55a29d2378f5d57785
Source dataset: uspto-grants-1989_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04863958

Reaction notes

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