Trifluoromethanesulfonic acid → HCID 66760033, compound

HRID 2063808Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([CH3:10])=[CH:5][C:4]=1[OH:11].FC(F)(F)S(O)(=O)=O>CCCCCCC>[CH3:1][O:2][C:3]1[C:4]2[O:11][C:6]([CH3:10])([CH3:7])[CH2:5][C:5]=2[C:6]([CH3:10])=[CH:7][C:8]=1[CH3:9]

Participants

Conditions

Temperature: 55 °C

Procedure

Further, by using 2-methoxy-3,5-dimethylphenol (7.60 g, 41.7 mmol), synthesis was also performed according to the following method. That is, to a solution of n-heptane (76 mL) containing 2-methoxy-3,5-dimethylphenol (7.60 g, 41.7 mmol) and isobutyl aldehyde (5.71 mL, 62.6 mmol), trifluoromethanesulfonic acid (1.85 mL, 20.9 mmol) was added dropwise, and the mixture was stirred at 55° C. for 2.5 hours. After cooled to room temperature, the reaction solution was washed with water and dried using anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by basic silica gel chromatography (hexane-ethyl acetate 100:0) and silica gel chromatography (hexane-ethyl acetate 100:0-95:5) to give 8.70 g of the title compound (yield 100%).

Workup

additionwas added dropwise
temperatureAfter cooled to room temperature
washthe reaction solution was washed with water
customdried
customthe solvent was removed under reduced pressure
customThe obtained residue was purified by basic silica gel chromatography (hexane-ethyl acetate 100:0) and silica gel chromatography (hexane-ethyl acetate 100:0-95:5)

Sources & evidence

ORD record: ord-78a81315e514446cb533775db84479ca
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288390B2

Reaction notes

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