Water → HCID 46311160, compound

HRID 1485074Notes

Reaction equation

HRID 1485074 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[C:12]([F:15])([F:14])[F:13])[C:5]([O:7][CH3:8])=[O:6].[H-].[Na+].[CH3:18]I.O>CN(C)C=O>[CH3:18][O:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[C:12]([F:13])([F:14])[F:15])[C:5]([O:7][CH3:8])=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 15109490Benzoic acid, 3-hydroxy-4-(trifluoromethyl)-, methyl ester

Product 1

HCID 46311160HCID 46311160, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 3-hydroxy-4-(trifluoromethyl)benzoate (see WO 2007/129745) (2.00 g) in N,N-dimethylformamide (9.00 mL), sodium hydride (60% dispersion in mineral oil, 545 mg) was added in small portions under cooling with ice. After stirring the mixture at room temperature for 30 minutes, methyl iodide (0.849 mL) was added. After stirring the reaction mixture at room temperature for 2.5 hours, iced water was added and two extractions were conducted with ethyl acetate. The combined organic layers were washed with water three times and thereafter dried over anhydrous magnesium sulfate. After removing the desiccant by filtration, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=95:5-85:15) to give methyl 3-methoxy-4-(trifluoromethyl)benzoate as a colorless solid (2.11 g).

Workup

  1. temperatureunder cooling with ice
  2. stirringAfter stirring the reaction mixture at room temperature for 2.5 hours
  3. extractiontwo extractions
  4. washThe combined organic layers were washed with water three times
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customAfter removing the
  7. filtrationdesiccant by filtration
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=95:5-85:15)

Sources & evidence

ORD record
ord-a69ae5559a1144dbbd40f9835f5f81bc
Source dataset
uspto-grants-2016_08
Patent number
US09422240B2

Reaction notes

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