Phenylmethyl 6-chloro-2-(4,6-dimethoxy-1,3,5-triazin-2-yloxy)benzoate → 2-Chloro-6-(4,6-dimethoxy-1,3,5-triazin-2-yloxy)benzoic acid

HRID 1885970Notes

Reaction equation

HRID 1885970 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([O:10]CC2C=CC=CC=2)=[O:9])=[C:6]([O:18][C:19]2[N:24]=[C:23]([O:25][CH3:26])[N:22]=[C:21]([O:27][CH3:28])[N:20]=2)[CH:5]=[CH:4][CH:3]=1>C(O)C.C(O)(=O)C.[Pd]>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([O:18][C:19]2[N:20]=[C:21]([O:27][CH3:28])[N:22]=[C:23]([O:25][CH3:26])[N:24]=2)[C:7]=1[C:8]([OH:10])=[O:9]

Participants

5

Reactant 1

HCID 11837546Phenylmethyl 6-chloro-2-(4,6-dimethoxy-1,3,5-triazin-2-yloxy)benzoate

Product 1

HCID 147736952-Chloro-6-(4,6-dimethoxy-1,3,5-triazin-2-yloxy)benzoic acidYield 83.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

A solution of 0.6 gram (0.001 mole) of phenylmethyl 6-chloro-2-(4,6-dimethoxy-1,3,5-triazin-2-yloxy)benzoate in 50 mL of ethanol and 15 mL of acetic acid was hydrogenated in the presence of 5% palladium on charcoal using a Parr hydrogenation apparatus. Upon completion of the hydrogenation, the reaction mixture was filtered through diatomaceous earth. The diatomaceous earth filter cake was washed with tetrahydrofuran. The combined filtrate and wash was concentrated under reduced pressure to a residue. The residue was dissolved in 150 mL of methylene chloride and was washed with two 150 mL portions of an aqueous solution saturated with sodium chloride. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was stirred in 10 mL of diethyl ether containing a few drops of heptane. The resultant solid was collected by filtration and was washed with cold diethyl ether to yield 0.26 gram of 2-chloro-6-(4,6-dimethoxy-1,3,5-triazin-2-yloxy)benzoic acid. The nmr spectrum was consistent with the proposed structure.

Workup

  1. filtrationUpon completion of the hydrogenation, the reaction mixture was filtered through diatomaceous earth
  2. filtrationThe diatomaceous earth filter cake
  3. washwas washed with tetrahydrofuran
  4. washThe combined filtrate and wash
  5. concentrationwas concentrated under reduced pressure to a residue
  6. dissolutionThe residue was dissolved in 150 mL of methylene chloride
  7. washwas washed with two 150 mL portions of an aqueous solution saturated with sodium chloride
  8. dry with materialThe organic layer was dried with magnesium sulfate
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated under reduced pressure to a residue
  11. filtrationThe resultant solid was collected by filtration
  12. washwas washed with cold diethyl ether

Sources & evidence

ORD record
ord-c2201d6be91e455bbd4bfbc411eca8d9
Source dataset
uspto-grants-1992_09
Patent number
US05149357

Reaction notes

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