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

HRID 1245184Notes

Reaction equation

HRID 1245184 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[C:8]([C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)=[C:9]([CH:14]=[CH:15][CH:16]=1)[C:10]([O:12]C)=[O:11]>[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[C:8]([C:17]2[CH:18]=[CH:19][N:20]=[CH:21][CH:22]=2)=[C:9]([CH:14]=[CH:15][CH:16]=1)[C:10]([OH:12])=[O:11]

Participants

5

Reactant 1

HCID 21919153Methyl 3-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-(4-pyridyl)benzoate

Product 1

HCID 219191873-(3,4,5,6-Tetramethoxy-2-methylbenzyl)-2-(4-pyridyl)benzoic acidYield 100%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

Methyl 3-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-(4-pyridyl)benzoate (301 mg, 0.5508 mmol) was dissolved in a mixed solution of a 1N aqueous solution of sodium hydroxide (10 ml) and 1,4-dioxane (10 ml) followed by stirring at room temperature for 16 hours. The reaction solution was diluted with water (100 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 (233 mg, 0.5508 mmol, 80%).

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-b5c6ff3f918b4f8b8da1a6f3e2e6dfdb
Source dataset
uspto-grants-2006_10
Patent number
US07122543B2

Reaction notes

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