Hydrochloric Acid → HCID 22054154, compound

HRID 1830245Notes

Reaction equation

HRID 1830245 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:34])=[C:5]([C:25]([O:32][CH3:33])=[C:26]([O:30][CH3:31])[C:27]=1[O:28][CH3:29])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=2)=[C:11]([CH:16]=1)[C:12]([O:14]C)=[O:13].Cl>[OH-].[Na+].O1CCOCC1.O>[CH3:1][O:2][C:3]1[C:4]([CH3:34])=[C:5]([C:25]([O:32][CH3:33])=[C:26]([O:30][CH3:31])[C:27]=1[O:28][CH3:29])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][N:22]=[CH:23][CH:24]=2)=[C:11]([CH:16]=1)[C:12]([OH:14])=[O:13]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 22054297HCID 22054297, compound

Product 1

HCID 22054154HCID 22054154, compoundYield 86%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

Methyl 5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-(4-pyridylmethyloxy)benzoate (0.600 g, 1.28 mmol) was dissolved in a mixed solution of an aqueous 1N NaOH solution (3 ml) and 1,4-dioxane (3 ml) and the resulting solution was stirred at room temperature for 6 hours. The reaction solution was diluted with water, rendered acidic with concentrated hydrochloric acid and then extracted with ether. The extract was washed with water and then dried, and the solvent was removed by distillation. The obtained residue was purified by silica gel column chromatography (hexand:ethyl acetate=1:2) to obtain the titled compound (0.500 g, 1.10 mmol, 86%).

Workup

  1. extractionextracted with ether
  2. washThe extract was washed with water
  3. customdried
  4. customthe solvent was removed by distillation
  5. customThe obtained residue was purified by silica gel column chromatography (hexand:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-263ffe4888034597bc0d797dcc17d365
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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