Hydrochloric Acid → 3-(2,6-Dimethylbenzyloxy)phenylpropionic acid

HRID 1925231Notes

Reaction equation

HRID 1925231 reaction equation
[CH3:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:12]([CH3:18])[C:13]([O:15]CC)=[O:14])[CH:9]=[CH:10][CH:11]=1.[OH-].[Na+].Cl>C(O)C>[CH3:23][C:19]1[CH:20]=[CH:21][CH:22]=[C:2]([CH3:1])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:12]([CH3:18])[C:13]([OH:15])=[O:14])[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66874894HCID 66874894, compound

Product 1

HCID 578227133-(2,6-Dimethylbenzyloxy)phenylpropionic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of Ethyl 2-(3-(2,6-dimethylbenzyloxy)phenyl)-2-methylacetate (Step C, 3 g, 9.6 mmol) in absolute ethanol (60 ml) was added 1N NaOH (20 ml) at room temperature. The reaction mixture was stirred for 3 hours, acidified to pH 3.5-4.0 by 1N HCl, and concentrated. The residue was taken into chloroform and washed with 0.1N HCl, 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.

Workup

  1. concentrationconcentrated
  2. washwashed with 0.1N HCl, brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by flash chromatography on a silica gel column (chloroform:methanol 95:5 spiked with acetic acid)

Sources & evidence

ORD record
ord-c7a727a4129144b09668e0b3be3db1bb
Source dataset
uspto-grants-2012_05
Patent number
US08178675B2

Reaction notes

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