Sodium Bicarbonate → HCID 23114127, compound

HRID 1787128Notes

Reaction equation

HRID 1787128 reaction equation
[CH3:1][C:2]1[C:20]([CH3:21])=[CH:19][CH:18]=[CH:17][C:3]=1[O:4][C:5]([CH3:16])([CH3:15])[CH:6]([C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)O.FC(F)(F)S([O-])(=O)=O.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[CH3:15][C:5]1([CH3:16])[CH:6]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[C:17]2[CH:18]=[CH:19][C:20]([CH3:21])=[C:2]([CH3:1])[C:3]=2[O:4]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2758875TrifluoromethanesulfonateHCID 23113876HCID 23113876, compound

Product 1

HCID 23114127HCID 23114127, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-(2,3-dimethylphenoxy)-2-methyl-1-(4-methylphenyl)propane-1-ol synthesized in Reference Example 135 (17.0 g, 60 mmol) in toluene (200 mL) was added trifluoromethanesulfonate (0.53 mL, 6 mmol) at 0° C., and the mixture was warmed to 50° C. The mixture was stirred at the same temperature for 30 minutes and was reacted under reflux condition for 2 hours. The reaction solution was cooled to 0° C., and then was poured into a saturated sodium hydrogen carbonate solution. The organic layer was separated, washed with a saturated brine, and dried over sodium sulfate, and the solvent then was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9) to obtain 9.3 g (yield 58%) of the title compound as an oily matter.

Workup

  1. customwas reacted
  2. temperatureunder reflux condition for 2 hours
  3. temperatureThe reaction solution was cooled to 0° C.
  4. customThe organic layer was separated
  5. washwashed with a saturated brine
  6. dry with materialdried over sodium sulfate
  7. distillationthe solvent then was distilled off under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9)

Sources & evidence

ORD record
ord-3b9d43123ec34e4f93e9ad96c6fa974a
Source dataset
uspto-grants-2009_03
Patent number
US07507841B2

Reaction notes

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