Methanol → HCID 15106503, compound

HRID 982234Notes

Reaction equation

HRID 982234 reaction equation
[OH-].[Na+].[C:3]([C:6]1[CH:18]=[CH:17][C:9]([O:10][CH2:11][C:12]([O:14]CC)=[O:13])=[C:8]([NH:19][C:20](=[O:38])[C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[CH:23][CH:22]=2)[CH:7]=1)(=[O:5])[CH3:4].CO.O1CCCC1>O>[C:3]([C:6]1[CH:18]=[CH:17][C:9]([O:10][CH2:11][C:12]([OH:14])=[O:13])=[C:8]([NH:19][C:20](=[O:38])[C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)=[CH:23][CH:22]=2)[CH:7]=1)(=[O:5])[CH3:4]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 15106490HCID 15106490, compound

Product 1

HCID 15106503HCID 15106503, compoundYield 82.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 1N sodium hydroxide aqueous solution was added to a mixture of 0.5 g of ethyl 4-acetyl-2-[p-(4-phenylbutoxy)benzamido]phenoxyacetate obtained in Example 53, 5 ml of methanol and 5 ml of tetrahydrofuran and the mixture was stirred at room temperature for 2 hours. To the reaction mixture was added 10 ml of water. The mixture was concentrated under reduced pressure to remove methanol and tetrahydrofuran. Diluted hydrochloric acid was added to the residue to render acidic. The formed crystals were taken by filtration and recrystallized from isopropyl alcohol to obtain 0.39 g of 4-acetyl-2-[p-(4-phenylbutoxy)benzamido]phenoxyacetic acid.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customto remove methanol and tetrahydrofuran
  3. additionDiluted hydrochloric acid was added to the residue
  4. filtrationThe formed crystals were taken by filtration
  5. customrecrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-a8ab127e3b0d41acadab7544b0749466
Source dataset
uspto-grants-1991_02
Patent number
US04994479

Reaction notes

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