Hydrochloric Acid → HCID 15106482, compound

HRID 1197096Notes

Reaction equation

HRID 1197096 reaction equation
[OH-].[K+].[CH3:3][C:4]1[CH:16]=[CH:15][C:7]([O:8][CH2:9][C:10]([O:12]CC)=[O:11])=[C:6]([NH:17][C:18](=[O:36])[C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:21][CH:20]=2)[CH:5]=1.Cl>>[CH3:3][C:4]1[CH:16]=[CH:15][C:7]([O:8][CH2:9][C:10]([OH:12])=[O:11])=[C:6]([NH:17][C:18](=[O:36])[C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)=[CH:21][CH:20]=2)[CH:5]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 15106474HCID 15106474, compound

Product 1

HCID 15106482HCID 15106482, compoundYield 79.5%

Conditions

Temperature
55 °C

Procedure

To 20 ml of a 10% potassium hydroxide-90% methanol solution was added 1.5 g of ethyl 4-methyl-2-[p-(4-phenylbutoxy)benzamido]phenoxyacetate obtained in Example 24 followed by stirring at 50 to 60° C. for 1 hour. After adding ml of a saturated saline aqueous solution, the reaction mixture was rendered acidic with diluted hydrochloric acid followed by extraction with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate to obtain 1.12 g of 4-methyl-2-[p-(4-phenylbutoxy)benzamido]phenoxyacetic acid.

Workup

  1. additionAfter adding ml of a saturated saline aqueous solution
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-d9161489f29441eaaefe96c16ed275df
Source dataset
uspto-grants-1992_05
Patent number
US05116853

Reaction notes

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