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

HRID 516833Notes

Reaction equation

HRID 516833 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-e8d3091c8d1a4b4ca9ff2806576b3bd7
Source dataset
uspto-grants-2015_08
Patent number
US09115072B2

Reaction notes

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