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

HRID 1850368Notes

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-faab9c3e81e3446e99f5c97dc539fbfb
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957069B2

Reaction notes

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