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

HRID 1245182Notes

Reaction equation

HRID 1245182 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]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[O:23][CH3:24])=[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]([CH3:34])=[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]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[O:23][CH3:24])=[C:11]([CH:16]=1)[C:12]([OH:14])=[O:13]

Participants

5

Reactant 1

HCID 21919154Methyl 5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-(2-methoxyphenyl)benzoate

Product 1

HCID 121472865-(3,4,5,6-Tetramethoxy-2-methylbenzyl)-2-(2-methoxyphenyl)benzoic acidYield 93.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

Methyl 5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-(2-methoxyphenyl)benzoate (1.34 g, 2.8755 mmol) was dissolved in a mixed solution of a 1N aqueous solution of sodium hydroxide (20 ml) and 1,4-dioxane (40 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 (1.21 g, 2.6769 mmol, 93%).

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-c76f1c9a8d4048789f106b58cec3d170
Source dataset
uspto-grants-2006_10
Patent number
US07122543B2

Reaction notes

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