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

HRID 73447Notes

Reaction equation

HRID 73447 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-e14d871d439c4ada8ed73a179004a53a
Source dataset
uspto-grants-2014_09
Patent number
US08829058B2

Reaction notes

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