Sodium Hydroxide → 4-(3-(2,6-Dimethylbenzyloxy)phenyl)butyric acid

HRID 73457Notes

Reaction equation

HRID 73457 reaction equation
[CH3:1][C:2]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH2:12][CH2:13][CH2:14][C:15]([O:17]CC)=[O:16])[CH:9]=[CH:10][CH:11]=1.[OH-].[Na+]>C(O)C>[CH3:1][C:2]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])[CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66875682Ethyl 4-(3-(2,6-dimethylbenzyloxy)phenyl)butanoate

Product 1

HCID 219645274-(3-(2,6-Dimethylbenzyloxy)phenyl)butyric acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of Ethyl 4-(3-(2,6-dimethylbenzyloxy)phenyl)butanoate (Step B, 3.26 g, 10 mmol) in abs ethanol (60 ml) was treated with 1N NaOH (20 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-fd512661f94a498cbfecda762edf1cd1
Source dataset
uspto-grants-2014_09
Patent number
US08829058B2

Reaction notes

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