Sodium Hydroxide → 2-(3-(2,6-Dimethoxybenzyloxy)phenyl)acetic acid

HRID 73463Notes

Reaction equation

HRID 73463 reaction equation
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[C:4]=1[CH2:5][O:6][C:7]1[CH:8]=[C:9]([CH2:13][C:14]([O:16]CC)=[O:15])[CH:10]=[CH:11][CH:12]=1.[OH-].[Na+]>C(O)C>[CH3:24][O:23][C:19]1[CH:20]=[CH:21][CH:22]=[C:3]([O:2][CH3:1])[C:4]=1[CH2:5][O:6][C:7]1[CH:8]=[C:9]([CH2:13][C:14]([OH:16])=[O:15])[CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66875196Ethyl 2-(3-(2,6-Dimethoxybenzyloxy)phenyl)acetate

Product 1

HCID 445473132-(3-(2,6-Dimethoxybenzyloxy)phenyl)acetic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution Ethyl 2-(3-(2,6-Dimethoxybenzyloxy)phenyl)acetate (Step A, 6 g, 18.2 mmol) in absolute ethanol (100 ml) was added 1N NaOH (40 ml) at room temperature. The reaction mixture was stirred for 3 hours, or until all the starting material is gone, concentrated and diluted with chloroform and acidified by 1M HCl to bring the pH to 3.5-4. The organic layer was washed with brine, dried over Na2SO4, filtered, concentrated and purified by flash chromatography on a silica gel column (chloroform:methanol, 95:5 spiked with acetic acid) to give the title compound as white solid.

Workup

  1. concentrationconcentrated
  2. additiondiluted with chloroform
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by flash chromatography on a silica gel column (chloroform:methanol, 95:5 spiked with acetic acid)

Sources & evidence

ORD record
ord-b773cfb390334814aa32d372b17ec64f
Source dataset
uspto-grants-2014_09
Patent number
US08829058B2

Reaction notes

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