Hydrochloric Acid → 3-{4-[3-(4-Chloro-2-phenoxy-phenoxy)-phenoxy]-2-methyl-phenyl}-propionic acid

HRID 1822258Notes

Reaction equation

HRID 1822258 reaction equation
C[O:2][C:3](=[O:35])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=3[O:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH:14]=2)=[CH:8][C:7]=1[CH3:34].[OH-].[Na+].Cl>CO.O>[Cl:26][C:23]1[CH:24]=[CH:25][C:20]([O:19][C:15]2[CH:14]=[C:13]([CH:18]=[CH:17][CH:16]=2)[O:12][C:9]2[CH:10]=[CH:11][C:6]([CH2:5][CH2:4][C:3]([OH:35])=[O:2])=[C:7]([CH3:34])[CH:8]=2)=[C:21]([O:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:22]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 578942213-{4-[3-(4-Chloro-2-phenoxy-phenoxy)-phenoxy]-2-methyl-phenyl}-propionic acid methyl ester

Product 1

HCID 111906953-{4-[3-(4-Chloro-2-phenoxy-phenoxy)-phenoxy]-2-methyl-phenyl}-propionic acidYield 107.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 3-{4-[3-(4-chloro-2-phenoxy-phenoxy)-phenoxy]-2-methyl-phenyl}-propionic acid methyl ester (0.221, 0.452 mmol) in methanol (7 mL) is treated with 5 N NaOH (2 mL) and heated to reflux until saponification is completed. The mixture is cooled, and the solvent is removed in vacuo to afford a residue that is acidified with 1 N HCl. The mixture is diluted with water and extracted with ethyl acetate. The organic layer is dried (Na2SO4), and the solvent removed in vacuo to afford 0.230 g (100%) of the title compound. 1H NMR (400 MHz, CDCl3); MS (ES+) m/z mass calculated for C28H23O5Cl 474, found 475 and 477 (M+1 and M+3, 100%).

Workup

  1. temperatureheated
  2. temperatureto reflux until saponification
  3. temperatureThe mixture is cooled
  4. customthe solvent is removed in vacuo
  5. customto afford a residue that
  6. extractionextracted with ethyl acetate
  7. dry with materialThe organic layer is dried (Na2SO4)
  8. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-e6368353e7ef47f8adace7afbc5525aa
Source dataset
uspto-grants-2009_10
Patent number
US07608639B2

Reaction notes

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