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

HRID 73450Notes

Reaction equation

HRID 73450 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH2:12][C:13]([O:15]CC)=[O:14])[CH:9]=[CH:10][CH:11]=1.[OH-].[Na+]>C(O)C>[F:1][C:2]1[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH2:12][C:13]([OH:15])=[O:14])[CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66875326Ethyl 2-(3-(2,6-difluorobenzyloxy)phenyl)acetate

Product 1

HCID 445473122-(3-(2,6-Difluorobenzyloxy)phenyl)acetic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution Ethyl 2-(3-(2,6-difluorobenzyloxy)phenyl)acetate (Step B, 7.86 g, 24 mmol) in absolute ethanol (120 ml) was added 1N NaOH (50 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 washed with 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. 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 on a silica gel column (chloroform:methanol, 95:5 spiked with acetic acid)

Sources & evidence

ORD record
ord-d4fa2719a65440c8b41b530202a48d69
Source dataset
uspto-grants-2014_09
Patent number
US08829058B2

Reaction notes

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