Methane → Methyl 5-[(2-chloro-alpha,alpha,alpha-trifluoro-p-tolyl)oxy]salicylate

HRID 234839Notes

Reaction equation

HRID 234839 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:17]=[C:13]([C:14]([OH:16])=[O:15])[C:12]([OH:18])=[CH:11][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:19]([F:22])([F:21])[F:20].Cl.[OH-].[NH4+].[CH4:26]>CO.CO.O>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:17]=[C:13]([C:14]([O:16][CH3:26])=[O:15])[C:12]([OH:18])=[CH:11][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:19]([F:20])([F:21])[F:22]

Participants

7

Reactant 4

HCID 297MethaneHCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 867502335-[(2-Chloro-alpha,alpha,alpha-trifluoro-p-tolyl)oxy]salicylic acid

Product 1

HCID 86750234Methyl 5-[(2-chloro-alpha,alpha,alpha-trifluoro-p-tolyl)oxy]salicylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

A chilled solution of 5-[(2-chloro-α,α,α-trifluoro-p-tolyl)oxy]salicylic acid (148 g, 0.45 mol) in methanol is saturated with hydrogen chloride gas, warmed to and held at room temperature overnight and poured onto ice. The aqueous mixture is adjusted to about pH 7.5 with concentrated ammonium hydroxide solution and extracted with methylene chloride. The combined organic extracts are washed with saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate, treated with 10 g of silica gel, filtered and concentrated in vacuo to obtain a dark gum. The gum is dissolved in a methanol-water solution, treated with charcoal, filtered and crystallized to give the title product as an offwhite solid (102.3 g 66.2% mp 62°-64° C.).

Workup

  1. temperaturewarmed to and
  2. additionpoured onto ice
  3. extractionextracted with methylene chloride
  4. washThe combined organic extracts are washed with saturated sodium bicarbonate solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. additiontreated with 10 g of silica gel
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto obtain a dark gum
  10. filtrationfiltered
  11. customcrystallized

Sources & evidence

ORD record
ord-d9843dcd462242bd95e84e2bf8b0d39d
Source dataset
uspto-grants-1997_01
Patent number
US05596124

Reaction notes

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