Dimethylformamide → Benzene, 1,2,5-trimethyl-3-[(2-methyl-2-propenyl)oxy]-

HRID 2063777Notes

Reaction equation

Br[CH2:2][C:3]([CH3:5])=[CH2:4].CN(C=O)C.[CH3:11][C:12]1[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=1[OH:20].C(=O)([O-])[O-].[K+].[K+]>O.C(OCC)(=O)C>[CH3:18][C:17]1[CH:16]=[C:15]([CH3:19])[CH:14]=[C:13]([O:20][CH2:4][C:3]([CH3:5])=[CH2:2])[C:12]=1[CH3:11]

Participants

Conditions

Temperature: 80 °C

Procedure

3-bromo-2-methylpropene (29.8 g, 221 mmol) was added to a mixture of DMF (130 mL) containing 2,3,5-trimethylphenol (25.0 g, 184 mmol) and potassium carbonate (50.9 g, 368 mmol), and the resulting mixture was stirred at 80° C. for 15 hours. After cooled to room temperature, the reaction solution was distributed using ethyl acetate and water. The organic layer was washed with saturated saline, and then dried using anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate 50:1 to 9:1) to give 33.6 g of the title compound (yield: 96%) as an oily product.

Workup

temperatureAfter cooled to room temperature
washThe organic layer was washed with saturated saline
customdried
customThe solvent was removed under reduced pressure
customthe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate 50:1 to 9:1)

Sources & evidence

ORD record: ord-0b0af8442c0343858f8e3e677e48c7cf
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288390B2

Reaction notes

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