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

HRID 1534207Notes

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; 1.6 mmole) in dichloromethane (5 mL) cooled at 0° C. was added 2-(p-methoxy-benzyl)-3-methyl-4-hydroxy-5-propyl-benzofuran (100 mg; 0.32 mmoles). A red solution resulted. To this solution was added dropwise dichloromethylmethylether (87 Σl; 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-85150d2568524fd983ebed0a4d8badfb
Source dataset: uspto-grants-1992_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05087638

Reaction notes

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