1-(4-Methylphenyl)-2-(2,3,5-trimethylphenoxy)ethanone → 4,6,7-Trimethyl-3-(4-methylphenyl)-1-benzofuran

HRID 1787152Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][O:10][C:11]2[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([CH3:18])[C:12]=2[CH3:19])=[CH:4][CH:3]=1>O>[CH3:17][C:15]1[C:16]2[C:8]([C:5]3[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=3)=[CH:9][O:10][C:11]=2[C:12]([CH3:19])=[C:13]([CH3:18])[CH:14]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 1-(4-methylphenyl)-2-(2,3,5-trimethylphenoxy)ethanone obtained in Reference Example 163 (1.0 g, 3.73 mmol) and polyphosphoric acid (6.0 g) was stirred at 80° C. for one and half hours. Water was added to the reaction solution, which was extracted with ethyl acetate. The organic layer was washed with a saturated sodium hydrogen carbonate solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to obtain 770 mg (yield 83%) of the title compound. Melting point: 112-113° C. (ethyl acetate-methanol).

Workup

extractionwas extracted with ethyl acetate
washThe organic layer was washed with a saturated sodium hydrogen carbonate solution
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-c45fe905c66147d8b6899abe6b03f83c
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07507841B2

Reaction notes

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