Water → HCID 68108763, compound

HRID 385153Notes

Reaction equation

HRID 385153 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([O:13][C:14]([F:17])([F:16])[F:15])[C:11]=1[OH:12])[C:5]([O:7][CH3:8])=[O:6].[C:18](=O)([O-])[O-].[K+].[K+].COS(=O)(=O)OC.O>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([O:13][C:14]([F:15])([F:16])[F:17])[C:11]=1[O:12][CH3:18])[C:5]([O:7][CH3:8])=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 68108720HCID 68108720, compound

Product 1

HCID 68108763HCID 68108763, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 3-chloro-4-hydroxy-5-trifluoromethoxybenzoate (2.64 g) was dissolved in N,N-dimethylformamide (15 mL), and potassium carbonate (3.60 g) and dimethylsulfuric acid (1.64 mL) were added to the solution, and then the mixture was stirred at room temperature for 1 hour. Water was added to the reaction solution and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=9:1) to obtain the title compound (1.70 g) as a colorless oily substance.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-d55f57d6551441e98a8f452cae0d6d2b
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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