Sodium Hydroxide → 5-(3-(2,6-Dimethylbenzyloxy)phenyl)-5-oxopentanoic acid

HRID 516823Notes

Reaction equation

HRID 516823 reaction equation
[CH3:1][C:2]1[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:24]=[CH:25][CH:26]=1)[C:9]([CH:11]([CH2:17][CH2:18][C:19]([O:21]CC)=[O:20])C(OCC)=O)=[O:10].[OH-].[Na+]>CO>[CH3:31][C:27]1[CH:28]=[CH:29][CH:30]=[C:2]([CH3:1])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([C:9](=[O:10])[CH2:11][CH2:17][CH2:18][C:19]([OH:21])=[O:20])[CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66875332Diethyl 2-(3-(2,6-dimethylbenzyloxy)benzoyl)pentanedioate

Product 1

HCID 445473105-(3-(2,6-Dimethylbenzyloxy)phenyl)-5-oxopentanoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of Diethyl 2-(3-(2,6-dimethylbenzyloxy)benzoyl)pentanedioate (Step B, 1.66 g, 4.0 mmol) in methanol (50 ml) was added 1N NaOH (17 ml) at the room temperature. The reaction mixture was stirred for 14 hours or until all the starting material is gone, concentrated, diluted in chloroform, and washed with 1M HCl to bring the pH to 3.5 to 4. The organic layer was washed with brine, dried over Na2SO4, filtered, concentrated and purified by flash chromatography eluted with chloroform:methanol (95:5 spiked with acetic acid) to give the title compound.

Workup

  1. concentrationconcentrated
  2. additiondiluted in chloroform
  3. washwashed with 1M HCl
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by flash chromatography
  9. washeluted with chloroform:methanol (95:5 spiked with acetic acid)

Sources & evidence

ORD record
ord-ec8a5b681b794fa29840bca8acf5fb8a
Source dataset
uspto-grants-2015_08
Patent number
US09115072B2

Reaction notes

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