Hydrochloric Acid → HCID 15106526, compound

HRID 982236Notes

Reaction equation

HRID 982236 reaction equation
[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]([O:7][CH2:8][C:9]([O:11]C)=[O:10])=[C:5]([NH:15][C:16](=[O:34])[C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:19][CH:18]=2)[CH:4]=1.[OH-].[Na+].Cl>CO.O>[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]([O:7][CH2:8][C:9]([OH:11])=[O:10])=[C:5]([NH:15][C:16](=[O:34])[C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:19][CH:18]=2)[CH:4]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15106524HCID 15106524, compound

Product 1

HCID 15106526HCID 15106526, compoundYield 76.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

In 25 ml of 90% methanol was suspended 0.54 g of methyl 4-methoxy-2-[p-(4-phenylbutoxy)benzamido]phenoxyacetate obtained in Example 95. To the suspension wad added 10 ml of a 1N sodium hydroxide aqueous solution followed by stirring at 60° C. for 2 hours. The reaction mixture was diluted with 50 ml of water and the system was rendered acidic with 7 ml of 2N hydrochloric acid. Extraction was performed with ethyl acetate. After the organic layer was washed water and dried over anhydrous magnesium sulfate, the solvent was distilled off. The obtained solid was recrystallized from isopropyl alcohol to obtain 0.4 g of 4-methoxy-2-[p-(4-phenylbutoxy)benzamido]phenoxyacetic acid.

Workup

  1. extractionExtraction
  2. washAfter the organic layer was washed water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off
  5. customThe obtained solid was recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-14761f2bc8384e6aadf7e9869f8c16c9
Source dataset
uspto-grants-1991_02
Patent number
US04994479

Reaction notes

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