Trifluoromethanesulfonic acid → HCID 66760033, compound

HRID 1850399Notes

Reaction equation

HRID 1850399 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

4

Reactant 2

HCID 62406Trifluoromethanesulfonic acidHCID 64514463,5-Xylenol, 2-methoxy-2×

Product 1

HCID 66760033HCID 66760033, compoundYield 202.3%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

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

  1. additionwas added dropwise
  2. temperatureAfter cooled to room temperature
  3. washthe reaction solution was washed with water
  4. customdried
  5. customthe solvent was removed under reduced pressure
  6. 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-f701e01ed7074302b2dd7aaf0f68e0ba
Source dataset
uspto-grants-2015_02
Patent number
US08957069B2

Reaction notes

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