Methyl 5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-(4-pyridyl)benzoate → 5-(3,4,5,6-Tetramethoxy-2-methylbenzyl)-2-(4-pyridyl)benzoic acid

HRID 1245179Notes

Reaction equation

HRID 1245179 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:32])=[C:5]([C:23]([O:30][CH3:31])=[C:24]([O:28][CH3:29])[C:25]=1[O:26][CH3:27])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)=[C:11]([CH:16]=1)[C:12]([O:14]C)=[O:13]>[OH-].[Na+].O1CCOCC1.O>[CH3:1][O:2][C:3]1[C:4]([CH3:32])=[C:5]([C:23]([O:30][CH3:31])=[C:24]([O:28][CH3:29])[C:25]=1[O:26][CH3:27])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)=[C:11]([CH:16]=1)[C:12]([OH:14])=[O:13]

Participants

5

Reactant 1

HCID 21919120Methyl 5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-(4-pyridyl)benzoate

Product 1

HCID 121472835-(3,4,5,6-Tetramethoxy-2-methylbenzyl)-2-(4-pyridyl)benzoic acidYield 74,360,080%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

Methyl 5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-(4-pyridyl)benzoate (910 mg, 2.0823 nmol) was dissolved in a mixed solution of a 1N aqueous solution of sodium hydroxide (10.4 ml) and 1,4-dioxane (25 ml) followed by stirring at room temperature for 16 hours. The reaction solution was diluted with water (200 ml), washed with ether, acidified with concentrated hydrochloric acid and extracted with ether. The extract was washed with water and dried and the solvent was evaporated therefrom to give the title compound (655 mg, 1.5484 mmol, 74%).

Workup

  1. washwashed with ether
  2. extractionextracted with ether
  3. washThe extract was washed with water
  4. customdried
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-754703fe53704163967a0fe92e95e4ee
Source dataset
uspto-grants-2006_10
Patent number
US07122543B2

Reaction notes

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