Water → Methyl 3-methoxy-5-(trifluoromethyl)benzoate

HRID 1524589Notes

Reaction equation

HRID 1524589 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[C:5](O)=[O:6].CI.[C:17](=O)([O-])[O-].[K+].[K+].O.CN([CH:27]=[O:28])C>>[CH3:17][O:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[C:5]([O:28][CH3:27])=[O:6]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 27831463-hydroxy-5-(trifluoromethyl)benzoic Acid

Product 1

HCID 46311161Methyl 3-methoxy-5-(trifluoromethyl)benzoate

Procedure

3-Hydroxy-5-trifluoromethylbenzoic acid (2 g) was initially charged at RT in DMF (15 ml) while stirring, and admixed dropwise with methyl iodide (3.0 ml). After adding potassium carbonate (5.6 g), the mixture was stirred for 5 h and left to stand overnight. It was then admixed with water and extracted three times with MtB ether. The combined MTB ether phases were dried over sodium sulfate, filtered and concentrated. 2.29 g of the title compound were obtained.

Workup

  1. stirringthe mixture was stirred for 5 h
  2. waitleft
  3. extractionextracted three times with MtB ether
  4. dry with materialThe combined MTB ether phases were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4987a1ece2184cf085b346164d55b680
Source dataset
uspto-grants-2015_07
Patent number
US09079906B2

Reaction notes

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